


Dean In Hell

by Arianllyn



Series: Therapy [4]
Category: Supernatural
Genre: M/M
Language: English
Status: In-Progress
Published: 2020-09-27
Updated: 2021-02-20
Packaged: 2021-03-07 16:15:33
Rating: Not Rated
Warnings: Graphic Depictions Of Violence, Major Character Death, Rape/Non-Con
Chapters: 16
Words: 27,537
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26680495
Author URL: https://archiveofourown.org/users/Arianllyn/pseuds/Arianllyn
Summary: Basically, everything Alastair and the other demons did to Dean in Hell until Castiel managed to rescue him. There IS an actual story, with an actual plot!This is a prequel to "You're a Mean One, Mr. Winchester" but can be read before or after that story, or entirely independently. Takes place between the S3 finale episode and S4E1.Graphic descriptions of various forms of torture, rape, sex with no or dubious consent, sexual slavery, Stockholm Syndrome, etc. This is NOT a fun fic. This is literally Dean being tortured. This is WHY Dean needs therapy. If you don't like this kind of material, or think you might be triggered by it, please, don't read this. This entire fic will likely be NSFW. YOU HAVE BEEN WARNED.All artwork mine. Comments requested.There is absolutely NO schedule as to when I will update this. Expect new chapters when you see them.  ;)
Relationships: Alastair/Dean Winchester, Castiel/Dean Winchester
Series: Therapy [4]
Series URL: https://archiveofourown.org/series/1814179
Comments: 31
Kudos: 30





	1. It Begins

**Author's Note:**

> Welcome! Dean has touched on what happened to him in Hell in discussions with Cas and Mia, and in his therapy journal; here, we look at just what, exactly, happened to him. This will NOT be fun. It WILL be NSFW. You have been warned.

The hellhound cornered him on top of the table, and dragged him to the floor, ripping his chest and abdomen open from nipples to groin, as it took him down. Dean looked helplessly up at his brother, as he almost instantly bled out on the tile. 

Dean blinked, and he was no longer in that room with Sam and the demon Lilith, where, he assumed, Lilith was likely killing Sam even now. No, now, he was hanging from a meat hook through his right shoulder, his hands and ankles locked into heavy iron shackles. The - room? area? - that he was in appeared to be vast, with millions of yards of heavy iron chain running in all directions. The air was thick with smoke and heat, a black-and-red haze hanging about, though Dean couldn’t make out any walls anywhere. 

_Dean in Hell_

Oddly, he was still clothed in a t-shirt and jeans - though his flannel was gone, and the t-shirt was ripped - and his chest appeared to have been put back together. The hook through his shoulder hurt, but it was bearable. It wasn’t by any means comfortable to be hanging from chains attached to shackled wrists and ankles that kept his arms and legs spread wide, but, again, bearable. This was torture? Weird. He’d’ve thought it would’ve been worse.

If Lilith had killed Sam, too, then _he_ was likely here, somewhere.

“Sam? Sammy? Can you hear me? _Sam! Help!_ ”

No one responded. He continued to call out until his voice grew hoarse and his throat sore. He was horribly thirsty, but, again oddly, it wasn’t even all that hot. 

Was this really Hell? So far, it wasn’t living up to the advertising.

***

Dean dozed off and on. Now and then, he’d wake and try to call out again, to Sam, or to anyone. No one came. 

He thought it strange that he heard no other screams or cries - only his own. 

He was desperately parched. He was starting to think he might be willing to suck off a demon, if it meant getting his throat wet, and he was afraid that it might come to that.

He blinked, realizing his eyes were also getting rather dry, and suddenly found himself in a much smaller, much hotter, room. He was now bound to a rack, kind of strapped down to a full-length easel, stood up at about a forty-five degree angle, so half-standing, half-lying back, ankles strapped apart, with legs spread; his wrists were strapped in by his waist, at the moment, but movable. He heard a noise behind him, then a shuffling sound, like someone with a limp walking around him, and then there was a tall, slender man in front of him.

“Hello, Dean.” The man had a truly obnoxious nasally voice. It made Dean’s inner ear shiver like chalk squeaking on a blackboard. “My name is Alastair. As you may have guessed, I am a demon, and I’ll be your host here in Hell.”

“Great. Nice to meet you. Your accommodations suck ass, and your hospitality is seriously lacking.” 

Alastair laughed. “Oh, Dean. Such wit. Such a bon vivant. We’re going to have a good time, I can tell. Well, Dean, I have an offer to make to start us out, if you’re interested in a deal. I believe you’re here as the result of a deal, so I’m thinking you’ll enjoy negotiating.”

“I already sold my soul. What else can I possibly have that you want, dickwad?”

“True, I have your soul. But let me tell you what I’m prepared to offer you, Dean. Either I can start in to torture you - really rip you apart in every way imaginable, making it hurt beyond your wildest nightmares… or, you can get down off the rack right now.”

“And what would I have to do for this little deal? Nothing’s ever free.”

Alastair grinned. “Well, Dean, it so happens that I have been looking, for a very long time now, for an apprentice. Someone to whom I can teach my craft - torture, in all its varieties - and I think you’d be an excellent candidate for the job. You’re strong, smart, creative, you’ve killed all manner of monsters without hesitation, you’re accustomed to blood and gore, and finding the nasty bits in your hair the next morning. So, you can get down off the rack, if… you agree to put others’ souls on it, and torture them for me. What’d ya say, Dean-o?” Alastair asked, affably.

“Screw. You. You can stuff that offer where the sun don’t shine, and in case you’re wondering, that’s right straight up your ass.” Dean spat the words out, viciously.

Alastair giggled, as if truly tickled by Dean’s vehemence. “See? Perfect. You are just perfect for what I have in mind, Dean. Well, if you won’t agree, that’s… frustrating, but no matter. If you _want_ to be tortured, I’m certainly happy to comply.”

Alastair picked up a scalpel, and Dean made a small, sharp, derisive noise with his lips. “Pfft.” 

“Oh, trust me, Dean, you won’t feel a thing. At first. The cuts will be shallow. You won’t even bleed right away. But soon enough, you’ll start to feel the cumulative effect of a dozen, a hundred, a thousand tiny slices, as the pieces of you start to pile up on the floor. And eventually...you’ll be screaming. Now, let’s begin, shall we?” He stepped forward, and made the first incision.

Dean snorted his breath out and in sharply. As promised, he hadn’t felt it, exactly... yet he knew _exactly_ where the scalpel had entered his forearm and come back out, about an inch lower toward his wrist. 

“That’s right, Dean, that’s good. Breathe. You’ll want to breathe all through this. Don’t try to hold your breath, that won’t help you at all.”

Of course, Dean then had to try holding his breath. The mere suggestion by Alastair that something wouldn’t help gave the clear impression that it actually _would_ \- yet Dean found that Alastair hadn’t been lying.

“Oh, I’ll never lie to you, Dean. I want you as my apprentice. I truly do. I’m a master at this sort of work, but I’m very old. I’m not thinking I need to retire immediately, but I’d like the option, and I can’t even think about it until I have someone trained up who does the work as well as I.” A second slice of skin, and Dean shivered helplessly.

***

As promised, Dean was screaming long before Alastair removed the rest of his skin, his muscles, sliced his ligaments and tendons, and went at his bones with a hammer. But even in a heap of pieces on the floor, _Dean could not die, nor find any respite by becoming unconscious -_ **_he was already dead_ ** _._ He felt every single thing Alastair was doing to him.

And then, weirdly, Alastair waved his hand, and Dean started to _heal_. His bones knit themselves back together; the tendons and ligaments rejoined, strong and sinewy; the muscles repaired; and the skin came back together seamlessly to cover it all. In seconds, he was fine - as good as he’d been before Alastair had started, even the meat-hook-through-the-shoulder wound, good as new.

“Well, Dean. It’s been a long first day, hasn’t it? A good start. So, what do you think of my offer, now? You agree to put others’ souls on the rack and torture them under my tutelage, and you can get down off of it, permanently. What do you say, Dean-o?” Alastair seemed as if he were hanging on Dean’s every word.

“Screw. You.”

Alastair laughed, delighted. “Excellent! You truly live up to the Winchester reputation! Well, we’ll be back at it in the morning. For now, Dean, enjoy the dark.”

Dean suddenly found himself floating in nothingness, no sensations of being touched, no light, no sound. Total sensory deprivation. He’d once read an article about Soviet experiments in how long political prisoners could withstand sensory deprivation; many of them had died within a day or so, panicking to so great an extent that their hearts simply gave out. But of course, again, _he was already dead_. He might go a little crazy, but he wouldn’t die. He could deal with this. No big deal. He was fine.

He was Dean Fucking Winchester, and he would not give that bastard what he wanted.

***

Over the next few days, Alastair continued to personally work on Dean. They were always alone in the small room during the day, Dean was always alone in the sensory deprivation chamber at night. Each day, at the end of the day, Alastair made the same offer, and Dean gave the same response: “Screw. You.”

And then, on the fifth day, Dean wasn’t put on the rack; he was simply left in sensory deprivation. He realized that he’d been unconsciously counting the seconds between when he arrived in the chamber and when he was put back on the rack, to be able to estimate the time of the day/night cycles in Hell, and when nothing happened when he’d expected it to, he… cracked, just a little. 

He was tired. He missed Sam, and Bobby. He was afraid that Sam had been killed by Lilith, and was undergoing similar treatment. He was afraid that Sam hadn’t been killed, and was trying to make a deal to somehow free Dean - a deal that would put Sammy right where Dean was now. He was afraid that Sam hadn’t been killed, but _wasn’t_ trying to make a deal to free him. 

His heart pounding, his neck wet with sweat, he trembled in the void. He had no idea how long it went on, this time; he couldn’t keep count and had lost all sense of time.

And then he blinked, and found himself suddenly back on the rack, with Alastair somehow mid-slicing, a pile of skin and muscle already lying on the floor, Dean already screaming. But only a few seconds later, he was again in sensory deprivation, as if he’d never left, and he had to wonder if he’d simply imagined the rack in order to feel _anything_ again. A tear slid down his cheek, the first since he’d arrived in Hell. He tried to raise his hand to wipe it away, and realized two things: (1) he couldn’t, because his hands were restrained; and (2) he could _feel_ the restraints - and the tear. 

His eyes widened. Was he in sensory deprivation, or wasn’t he? Was he simply blind and deaf now? 

_What in the literal Hell is going on? Why can’t I see and hear?_

***

**Notes for the Chapter:**

> This is a mild start, basically just putting a certain framework for how Hell works - at the blink of an eye, without notice - in place. Alastair does some mild damage, and gets Dean screaming, but the worst of the torture here is the confusion Dean feels. Alastair wants Dean off-kilter.
> 
> Please comment! ;)


	2. New Tortures

**Summary for the Chapter:**

> Dean is tortured with pleasure, then sensory deprivation. He obeys commands as it becomes clear that he will be forced to anyway if he doesn't willingly... and then he's devoured by rats.

The inability to see and hear, yet being able to suddenly feel, strangely made Dean panic more than the ordinary total sensory deprivation had. 

And just as suddenly, that was over and he was lying on a soft bed, healed up, naked, and a beautiful woman was perched on the edge of the bed next to him. She smiled at him, and without thinking, Dean smiled back. She snapped her fingers, and Dean was bound to the bedposts. He struggled uselessly against the restraints.

“You might as well relax, Dean Winchester. I do not intend to hurt you. I wish to make you feel pleasure,” the woman told him, a slight Russian accent noticeable in her words. 

“Yeah, right,” Dean retorted, continuing to try to pull his wrists and ankles free.

“Truly. You have been through much this past week. Alastair has been harsh with you, yes? Let me make you feel _good_ , now.” She bent to kiss him; he tried to twist his face away, but she framed his face with her hands and held him still. “Do not struggle so much. I will treat you right, Dean Winchester.”

She kissed his lips gently, then slid down his body, her lips touching his skin in all the little spots guaranteed to make him shiver - neck, nipples, abdomen, groin, along the top of his rapidly-hardening cock - and then she wrapped her lips around the head and he threw his head back and cried out in pleasure. She smiled around him, and he felt the angle change slightly, as her tongue slid down his length even as she continued to suck lightly at the tip. He moaned.

_Maybe she means it. I don’t know why I’d get a sex break in Hell, but I’m not complaining so far!_

She wrapped her hand gently around the base of his cock, continuing to suck on the head, her other hand sliding under to lift and gently finger Dean’s balls. His back arched up off the bed, and he gasped for breath.

The gentle sucking grew slowly harder. Dean’s cock was hard enough now to hammer nails, precome leaking from the slit. Her tongue wiped over it to clean it away every so often in a gentle motion. 

It was all Dean could do to breathe, the pleasure was so intense. And all she was really doing, so far, was a blow job on the very end of his dick!

 _Why does_ **_this_ ** _feel so good?_

Her tongue inserted itself a short way into the tip of Dean’s cock, and it felt like an electric charge went surging up his length. He felt himself shuddering in abject pleasure, and it made no sense. She wasn’t doing enough to turn him on this much!

“Please,” he whispered. “Stop.”

She laughed lightly around his cock in her mouth, and took him a little deeper, her tongue gliding over the tip and then up and down his length. 

Dean arched helplessly, unable to relax or come down. The pleasure was rapidly turning to pain. She was barely touching him, her hands at his sides now, fingers gently rubbing at the skin just above his hips, only her lips and tongue really going at him with any kind of purpose that he’d describe as sexual, and yet his body was locked in a spasm, bowed about an inch off the bed.

“Please, stop!” he managed to gasp out a little louder. In response, she only took him deeper, sucking harder. He screamed in pleasure and in pain at once. Stimulated past the point of pain, yet he still couldn’t find his release.

And then, suddenly, he was back on Alastair’s rack, still naked. He shuddered, and came, twitching in the restraints as Alastair laughed, watching him.

“That, Dean, was a succubus. Did you like her?”

Dean could do no more than whimper in exhaustion.

Alastair picked up his favorite scalpel, and started to cut into Dean’s skin, and this time Dean felt it immediately. The pain engulfed him, and he screamed at the first slice that Alastair took. 

“That’s it, Dean. You feel _everything_ on that endorphin high. You feed the succubus, she gives you pleasure bordering on and sometimes passing well _into_ pain, and then you come to _me_ , and you can feel even the shallowest of cuts with about one hundred times more intensity than you ordinarily would. Sensory deprivation, straight to sexual over-stimulation, and from there, straight to cutting. And with the first slice, look at you; you’re already _screaming_ . I’m so proud. So, Dean, does it feel like Hell _now_ ? Are we ‘living up to the advertising’ now, _boy_?”

Dean sobbed, tears streaming, unable to hold back, as Alastair cut on him again and again.

***

Alastair cut Dean down to nothing, and ground his bones into paste, then set fire to the lot. And somehow, Dean still existed, could feel everything that Alastair did, and when Alastair waved his hand, chuckling, Dean’s body healed itself. This went against everything Dean had thought he knew about how spirits worked; if you burned the bones, they vanished into nothing, not subject to recall. Alastair saw his confusion.

“Dean, this isn’t your actual body, these aren’t your actual bones. I’m cutting into your soul. What you see is a physical representation of yourself that your mind persists in projecting. Demons that have turned to smoke no longer project their physical bodies; that’s why they need to take someone over by possessing them when they go topside. You’re far from a demon, boy. Your soul is still fairly pure, even though you sold it to us.”

Dean still looked suspicious. “You’re wondering why I’m explaining. I told you, Dean, I want you to be my apprentice, and eventually, my successor. By then, yes, you’ll be a demon. But it doesn’t make sense for me to lie to you now and then have to retrain you later. It’s far easier just to tell you the truth from the get-go. And why not? Even if you don’t take me up on my offer, it’s not like you can escape. I haven’t told you any secrets, here; just clarified things you already knew, really, but were just a little confused about. I mean, c’mon, Dean-o, if you’d thought about it for a while, I’m betting you’d have figured out that I’m not really cutting on your body, here, right? You’re no dummy. So if you’re just going to come to the same conclusions on your own anyway, why not just short-circuit the process and tell you myself? I told you, I won’t lie to you, Dean.”

“Of course you will. You’re a demon; demons lie.”

“I will admit, we do have that rather nasty reputation. But why would I lie to you, Dean? When I want you to be one of us so much? I want you to take over my job, Dean. I run the whole department, here, y’know. My title is ‘Grand Inquisitor of Hell,’ and I earned it. Took me centuries, had to prove myself to Lucifer himself. You’re lucky, Dean. You’re on the fast-track, and you only have to prove yourself to me - and I already think you’re the best candidate I’ve seen.

“So, Dean, ready to accept my offer and start torturing others’ souls for us, yet?”

Dean swallowed hard, gasping for breath, for a moment, then…. “Screw. You.” 

“Ah. Not yet. Well, have a good night, then, Dean.” And just like that, Dean was back in sensory deprivation, again.

***

This time, he was left in sensory deprivation for almost three weeks. He couldn’t feel anything, see anything, hear anything. He couldn’t taste his own spit, and couldn’t feel whether or not he was really running his tongue around his teeth like he imagined he was trying to do. There were no scents, here. All five senses, completely gone - useless. There was simply nothing to sense.

And then, sound. Footsteps? A key in a lock? A door, opening? A switch being thrown? And suddenly, he could see again, feel the floor beneath him.

“Kneel.”

Dean stayed put, determined not to comply with the commands tossed at him.

“Kneel, or you will be made to kneel.”

Dean continued to lay still. 

The sound of fingers snapping, and Dean was on his knees, head bowed low, hands on his thighs, palms facing up.

_Wait, what?_

“If you are not ready to obey simple commands, you can be returned to sensory deprivation until you are more… pliant. It is nothing to me. Ten years or twenty, sooner or later, you will be so desperate for sensory input that you will beg to be allowed to suck me dry, just for a simple touch. Pray to me for a light to see by. You already sense that this will be true for you very soon, Dean. Stand.”

Dean slowly rose to his feet.

“Good. Now, kneel, on your own, and willingly, in the position you were just in, or back into the dark you go.”

Dean knelt.

“Excellent.”

And just like that, Dean found himself back on Alastair’s rack, bound as usual, but now, Alastair wasn’t present.

Out of the corner of his eye, he noticed a small rodent in the corner. He’d read Burnett’s _The Little Princess_ to Sam as a child, and remembered the story of Melchisedec, the rat in the attic who befriended the orphaned Sara Crewe. He chucked and spoke quietly to the rodent, and it looked at him inquisitively. It came closer, and he smiled encouragingly. The rodent looked at him, and seemed to examine him up and down. The rat ran off, and Dean felt disappointed, for a moment. 

But then, the rodent returned… with a large number of its friends. As Dean whimpered and squirmed, then screamed, in terror, the rodents swarmed him and devoured him, one tiny bite at a time, down to his bones.

Only when the last rat was gone did Alastair appear. He waved his hand, and Dean shuddered, whole again.

“So, Dean. Ready to take me up on my offer, yet?” Alastair asked, grinning.

“Screw. You. _Asshole_.”

***

**Notes for the Chapter:**

> Again, Alastair is keeping Dean off-kilter, trying to break him down slowly. As far as Alastair's concerned, he has all the time in the world, here. 
> 
> Please comment. ;)


	3. Competition

**Summary for the Chapter:**

> Dean learns his lessons, but continues to reject Alastair's offer. Alastair invites the other candidates for the position of his apprentice to compete by torturing Dean and lets Dean sleep a bit for a change. The first candidate, a smoke demon, rapes Dean and carves words into Dean's back. Once he's gone, Alastair rapes Dean as well. Then Dean returns to sensory deprivation, while Alastair takes a shower, then gets to work in his workshop creating false memories to be implanted into Dean the next time he's rebuilt.

Sensory deprivation lasted slightly longer each time, he thought. Each time now, he strained to hear the footsteps that were the first indication that someone was coming to release him from what appeared to be - well, some kind of spell, was Dean’s best guess. One second there was complete nothingness, no input for any of the five senses, and the next, he’d hear it. “Thup thup thup thup” - someone walking toward the door. “Jangle” - keys. “Scrape” - the key being put into the lock. “Fwoosh” - the door opening. And then his other senses would return, and he would fall to his knees and assume the position he’d been taught early on - ankles crossed, knees spread wide, hands resting lightly on his thighs, palms up, head low, eyes down. 

He was never sure who the torturer would be, when they came this time - Alastair, the succubus whose name he was never given and was afraid to ask, or one of the other myriad of demons that Alastair used on a somewhat rotating basis to keep his torture fresh - but he had learned quickly that his failure to kneel, before the torturer even had a chance to give the command, meant more pain than simply (and literally) falling into compliance. No matter how dizzy the sensory deprivation left him, he had to get into and keep the position perfectly, without swaying or putting his hands to the floor to catch himself, without ever looking up unless told to do so, and without ever -  _ ever  _ \- trying to protect any part of his body that his torturer might want to explore that day.

His mouth? He’d offer it up. He was kept so horrendously parched that, as he’d feared at the start, he was willing to do  _ anything _ for a drop of moisture in his arid throat, including sucking off Alastair or the other male demons. They didn’t want him that way often enough to come near slaking his thirst.

His ass? So far, no one had wanted it for anything beyond turning it bright red, or cutting the meat straight off the bone, but he assumed that at some point anal rape would likely make its way to the table. Just because Alastair hadn’t wanted it yet, and the succubus only ever wanted to suck on his cock until he screamed, didn’t mean that his ass wouldn’t get thoroughly plowed eventually. He expected it, and was relieved each time when it didn’t yet occur.

His cock? The succubus could have it; he hated the overstimulation, but it was just one more thing in a long list of horrible things that happened to him here on a fairly regular basis. Alastair didn’t seem to have much use for it, other than as one more thing from which to slice skin and muscle.

The rest of him? Well, that just involved pain. And Dean Fucking Winchester could handle pain.

But dear sweet God, he was tired.

***

Alastair waved his hand, and Dean was healed and once again bound to the rack.

“So, Dean. How about today, then? Will you take my offer? I’ll throw in a quart of Gatorade, what d’ya say?”

Dean retched. Dry heaves. Again. Then, slowly and quietly, came, “Sc...rew… You... “

“So be it.” Alastair clicked his tongue, sounding slightly annoyed. “Well, if you’re  _ sure  _ you’re not going to take the offer - I mean, it’s still open to you, Dean, I  _ really  _ want you on board,  _ eventually  _ \- I guess I’ll have to start thinking alternative arrangements. I mean, I’m going to have to retire some day. And when I do, I need a replacement in place. I can’t wait to start thinking about this  _ then _ . 

“I know, Dean! I’ll invite the other candidates - demons, all, by the way - in and have them torture  _ you _ and we’ll see who the most creative one amongst them truly is. You can help me judge. Yes? Wonderful. I’ll let them know to come tomorrow, bright and early.”

***

Alastair left Dean bound to the rack, which meant that Dean actually got a modicum of sleep, finally. His brain felt fried from lack of sleep, but, as with everything else, it couldn’t really harm him, it was just an annoyance. But when he needed to be sharp for a new torturer, it was an annoyance that could be costly.

The first “candidate” was a vessel-less smoke demon. Dean was vaguely amused by the idea of a wisp of smoke harming him, since Dean’s soul could not be possessed, being itself bodyless. Until, that is, the smoke demon had two of its friends hold Dean down, bent over a table, his legs spread wide, arms pinned behind his back, face held taut against the table. And then the smoke demon proceeded to rape Dean’s ass.

He would not have thought that it would feel like much for a smoke demon to enter him, but somehow, it was horrid. He could feel it absolutely everywhere, no flesh at all, just pressure on every possible contact point, to the point of pain, like it was twenty times bigger than the largest person he could ever have imagined going in there - had he imagined that. And what was worse, now he knew that he  _ had _ imagined that, but had gotten it all wrong.

_ Good thing Dad’s already dead, because finding out that I had ever even so much as  _ **_thought_ ** _ about that would have sent him over the edge. _

And then he wondered where  _ that  _ notion had come from.  _ His  _ father? His mild-mannered-though-drunk-when-present, almost-always-absent, father? John Winchester had been many things, but Dean didn’t believe for a second that homophobic had been amongst them. So, why had that errant thought flitted across his brain just then?

And then the demon began to move inside him, and it was like there were a thousand sharp barbs on the cock that didn’t even exist, pricking Dean as the demon slid back and forth, more easily with each pass, as more of the skin there was abraded away by the violent thrusting.

Dean closed his eyes. If he could just get away in his mind to anywhere else… but no, the demon kept changing up his pace, and Dean couldn’t adjust quickly enough to lose himself in any sort of rhythm. The tears started, and Dean couldn’t stop them. The demon moved faster in response, and if a smoke trail could have laughed, it would have been.

The point didn’t seem to be release for the smoke demon (and just how much release could a puff of smoke get, anyway?), but rather Dean’s humiliation. The demon, rightfully guessing that making Dean cry was as good as it was going to get, pulled out, but the other two demons didn’t release their hold on Dean. 

Instead, the smoke demon picked up a scalpel and went to work, carving words into the flesh of Dean’s back. When it was finished, it stood back to admire its handiwork, and Alastair came over to read the message. “I’m a smoke demon’s bitch.” Dean sobbed involuntarily, trying to catch his breath, and Alastair laughed.

“Well, Tony, you’ve done well. I’ll be in touch about my decision regarding the position, but in the meantime, I believe you’ve earned a reward. Go on up topside, and find yourself a meat suit. Get a nice young one, now, built to last, eh?” Alastair grinned and the three smoke demons disappeared out through a vent.

Dean half-lay on the table, shuddering. Alastair shrugged. “Normally, I wouldn’t bother, Dean, but since you look so pretty, laying there like that, all stretched out….”

Dean screamed as Alastair pushed into him dry. He rode Dean hard, and then, when he was finished, Dean found himself in sensory deprivation once again - with the single difference that he could feel every bruise, and the sticky sensation of Alastair’s ejaculate as it dripped out of his anus and down his leg.

***

_ Alastair _

Alastair took a nice hot shower, and put on a fresh shirt and pants, then went to his workshop, and got to work. He sifted through the memories he’d carefully lifted from Dean the day before, and created new ones, similar, but with an accent on John Winchester’s treatment of his eldest son. 

No one would accuse John Winchester of being a perfect father; in fact, he’d been neglectful of his sons to the point of child abuse. And Dean had borne the brunt of that neglect, trying to spare his younger brother. The memories of the neglectful abuse were real, but Alastair sharpened the memories of John’s alcoholism, created new memories of John’s physical abuse of Dean, of beatings with fists and with belt, and also created new memories of alternate events, where in the real memory, John had, say, told Dean that there were lots of ways to earn money, then taught him to hustle pool, but in the new memories, John told Dean that there were lots of ways to earn money, and then pimped him out to a buddy at a truck stop for $50. 

Alastair put all the memories into individual envelopes, which he carefully labeled; it wouldn’t do to make a mistake when rebuilding someone’s psyche, particularly not someone he needed as much as he needed Dean. Insertion of new memories was a delicate process, but here, Alastair didn’t intend to replace the old memories, but simply to supplant them. When he was done, Dean would remember his childhood as a kaleidoscope of blurry images, never able to focus on the real, true memory, despite it being right there in his mind. Confusion and a desire to be nothing like his abusive father would motivate Dean to comply with Alastair’s wishes, and accept his offer.

It really was  _ such  _ a generous offer.

***

**Notes for the Chapter:**

> Remember that Dean was downstairs for approximately forty years, Hell time. By the end of this chapter, he's been in Hell about two months of that forty years. There's a long way to go, yet.
> 
> Please comment! ;)


	4. The Second Candidate - Meg

**Summary for the Chapter:**

> Dean thinks while in sensory deprivation. He's returned to sensory input for the next candidate's "audition" to find that it's Meg. Meg makes him dance for her while being electrocuted, then perform oral sex on a nun to remove the painful mesh of a chastity belt from the poor woman.

**Notes for the Chapter:**

> TW - electrocution, forced oral sex, whipping with a riding crop, chains, shackles, and other metal torture implements worn, chastity belt.

Dean slowly grew to love being in sensory deprivation. He knew it was meant to be just another form of torture, but it had no real effect on him. He was supposed to panic, but instead, he just felt very calm and relaxed. He couldn’t die from it, after all - he was already dead. 

While in SD, Dean could think his own thoughts, he could doze, he could dream - and Alastair and the rest of his merry band of torturers couldn’t stop him, because to stop him would mean they’d have to give him some sort of sensory stimulation. They’d have to pay attention. 

He spent a lot of SD time lost in his memories, particularly replaying conversations he’d had with Sammy. Good Lord, he missed his brother. He had never learned whether Sam was still alive, or if he’d been killed by Lilith the same night Dean had been taken out by her hellhound. He was afraid to ask.

He also thought a lot about Alastair and this offer he kept making. Why? Why was it important that Dean become the Inquisitor’s Apprentice? (Side question - would he get to make brooms and mops dance to Tchaikovsky if he did?) He was determined not to give in, if for no other reason than he just wouldn’t give that nasally son of a bitch the satisfaction.

***

The next candidate came in, saw Dean in position on his knees, and started laughing. 

“Dean Winchester. Really? Oh, this’ll be fun.”

“Careful, Meg. He’s a candidate, too. He’s just a little reluctant to accept that fact, as yet.” Alastair smirked.

“Full disclosure, Alastair; I’ve got… history with Dean, and his brother. You got Sam stashed here somewhere, too? I could make it a twofer.” Meg grinned.

“Let’s just see your audition piece, Meg.” Alastair took a seat, and watched, a clipboard in his hand.

“Fine.” She turned her attention to Dean. “On your feet, boy.”

Dean kept his eyes down, but rose from the floor to his feet. Meg ran a gentle finger around his neck, drawing a line around it, and as she drew, a leather collar came into being, eventually locking itself around his neck. Meg’s finger moved to his chin, and tipped it upward, forcing him to look at her.

“Hey, Dean. Not going to say hello?”

“Hey, Meg.” Dean dropped his eyes again.

“That’s it? That’s all I get from you? ‘Hey, Meg’? Wow. You’ll pay for that, Dean-o.” She waved her hand, and the leather collar became a metal shackle, instead. She attached it to a chain, and led Dean over to a metallic area of the floor, that looked like it might be a trap door. He hesitated to step on it, but she pushed him forward. She put metal cuffs on his wrists and ankles, and those had metal chains attached as well; she connected them, pulling them tight, Dean’s hands behind his back, so that he had to stand with feet together, his back arched, his shoulders already aching from the pull. No one had bothered to clothe Dean in quite a while; he’d lost track of how long he’d been naked, now. His hips were pushed forward by the chains, and Meg smirked at him as she quickly stroked his cock to hardness.

“That’s not for your pleasure, Dean,” she told him when he moaned quietly. “You’ll see.” She slipped a metal cock ring over his member, fastening it securely at its base, and ran a thin metal chain from it up to the collar around his neck. Then, Meg stepped back from the metal floor, back to the wooden area...and hit a button. 

Dean heard the electricity before he felt it, like a generator was whirring somewhere nearby, and then, suddenly, every cell in his body was jolted and sizzling. Where the chains, shackled, and cock ring were attached, his flesh burned; the soles of his feet on the metal floor were in agony, but falling to get off of them would only give other parts of his skin the same sort of burn wounds. He screamed. The power cut out, and he trembled, trying to keep still. Moving wouldn’t help anything, and might (1) hurt his feet more, and (2) anger Meg. Clearly, he’d already pissed her off more than enough.

“Like that, Dean?” Meg taunted. 

Dean gritted his teeth, but managed to stay silent.

“Kneel.”

Dean got down into his position, slowly, finding it harder with his hands behind him. Meg grinned, and hit the button again. Dean winced as he heard the generator, and screamed again when the voltage shot through him, his back arching helplessly, his hard cock punching up into the air. The power cut out, and he tried to relax, to catch his breath, and then he heard it, again, and then….

“Ahhhhhhhhhhhhhhhhhhhhh!” Dean screamed as it hit him again. The power cut out and he panted for air, trying to drag something into his lungs, which felt like they might be on fire.

“Stand up, Dean,” Meg commanded.

Dean tried, but couldn’t. His legs felt like rubber, the chains held his hands in place behind him so he couldn’t use his arms to leverage his way up. He whimpered in fear of being thought disobedient, but he couldn’t manage to rise.

“I said, stand up.”

“I can’t. Please, I need my hands to be able to rise from this position,” Dean tried reasoning with Meg.

She reached down and grabbed his left shoulder. She hauled him up from the floor. “That’s two, Winchester. Three strikes and you’re out.”

“I’m sor….”

“I don’t want to hear it. Now, you’re going to dance for me, monkey.” Meg unhooked the chains to his wrists, and fastened them to a bar hanging from the ceiling, so that Dean’s arms were above his head, and his body was forced to stretch significantly, his toes resting on the metal floor.

_Dean chained up by Meg_

Meg stepped back to the wood again. “Dance.”

She hit the switch. Dean heard the generator, and felt the electricity, but it was bearable this time. He pulled one leg up from the floor, then the other; he couldn’t get a complete respite from pain, but he could manage to obey Meg’s order - he was sure this was what she’d meant by the command to “dance.” Except the electricity didn’t stop this time, and he had to keep shifting his weight, wincing with each movement.

“Faster. Or should I up the voltage?” Meg grinned.

Dean started “dancing” faster, wanting to avoid additional pain as much as possible.

“Good boy. It _can_ be taught.” Meg laughed, amused by her own snarky comment.

The power finally cut out, and Meg stepped over and released Dean’s arms from the chains, but not from the metal shackles around his wrists.

“Kneel.” Dean fell to his knees, assuming the position he’d been taught.

Meg bent over and whispered in his ear. “I assume that you know how to pleasure a woman with your tongue, Winchester.” Dean grimaced, but nodded.

Meg caught the grimace, and laughed. “Oh, I didn’t mean me, Dean-o. Your tongue’s a bit too sharp for my liking, and you’re not my type. Sam, now, _he_ was my type.” She raised her voice to normal levels, and said, “You sure you don’t have Sammy here somewhere, Al? Because the best way to torture Dean here would be to not touch him, but torture Sam in front of him while he’s helpless to prevent it.” 

Dean looked up at her, at that, eyes dark and foreboding. Meg just laughed. “Cute little puppy. You can’t hurt me, Dean, so there’s no point in threatening looks - unless you’d like to dance some more for me? You _were_ awfully pretty.”

Dean dropped his eyes again, but his mind was whirling. Was Sam here? Or safe? And then….

_Wait. Why would she ask me about oral sex if she didn’t mean her? Who, then?_

“Now for the next part of my … ‘audition piece’, as Al put it. Crawl over here, Dean.” Meg pointed to a spot in front of an empty rack, an adjustable one, like the one Alastair usually used with Dean’s torture. Dean mentally shrugged, and did as he was told.

“Now then.” Meg snapped her fingers, and a terrified-looking nude woman appeared on the rack, bound to it, legs bound wide apart. Dean glanced up and could see chains extending from the woman’s groin up to a slightly wider chain around her waist. The smaller chains appeared to be pulled tight. “Your challenge, Dean, is this. This poor soul here has a dilemma. She’s locked into a chastity belt, poor thing. That’s what these are.” Meg fingered the smaller chains, and the woman whimpered, but whether in fear or arousal, Dean couldn’t tell without looking higher up than he figured he’d be allowed without punishment.

“These chains, and the ones in back that you can’t see at your present angle and line of sight, lead to a small piece of metal mesh that fits between her labia, Dean. It covers her vagina and clitoris, and I’m afraid it’s quite painful. Isn’t it, dearie?” This last was addressed to the woman, who nodded, eyes wide.

“So. Dean. Your task is to lick the chastity belt. With each lick of your tongue, a bit more of the mesh will flake away, so if you’re very thorough, and give this poor lady a good tongue bathing, she won’t be in pain anymore. You’ll be helping her, Dean-o.”

Dean looked up at Meg sharply, a question in his eyes that he didn’t dare to voice. Meg got it, though, and chuckled.

“How is this torture for you, Dean? Is that what you want to know? Well, here’s the thing. This poor soul, while she was alive, was a virgin nun. The chastity belt is a mockery, because she never wanted sex. She doesn’t want the pain for it, either, so you will be helping her in that sense - but she really doesn’t want your mouth anywhere near her poor little private parts. She’ll consider it rape. And I know that you prided yourself on never being with someone who didn’t want you. But here, you don’t have a choice, Dean-o. That’s how this tortures you. In order to help our poor little Sister, here, you have to rape her. Now, kneel up, and get to work.”

The nun shuddered. Already, tears were dripping down her cheeks and from her chin. Dean winced, but steeled himself, knelt up on his knees, and leaned forward carefully, then closed his eyes...and gasped as Meg brought a riding crop down across his shoulders.

“You have to keep your eyes open, Dean. You have to give her pleasure, and you’ll have to move quite a bit faster than that. Now, get busy.” The crop descended again, and Dean hissed in pain.

Dean leaned forward again, and did as bid, licking gently but trying to get his tongue everywhere he could feel the hard metal, taste the metallic tang of it, trying to do a good job to free the poor woman of the painful mesh. The crop came down across his back and shoulders at irregular intervals, and he had to work to ignore it, to simply continue to lick as fast as possible, so as to offend the Sister’s sensibilities as little as he could.

He didn’t want to know what a nun had done to land her in Hell. He just wanted to be free of this nightmare.

Meg really did know him a little too well.

***

**Notes for the Chapter:**

> Meg once told Dean (in the show) that she'd also served as Alastair's apprentice. 
> 
> Please comment!


	5. More Meg

**Summary for the Chapter:**

> Meg finishes her "audition" and gets her score from Alastair. Alastair puts Dean back on the rack for a challenge - if Dean doesn't start to bleed before the 100th cut Alastair makes on Dean's skin, Alastair will allow Dean to sleep. Dean wins, but before he can sleep, Alastair announces that there's a third candidate.

The nun hadn’t stopped crying since before he’d started, so her sobs were nothing to go by, but Dean couldn’t find anything else that either tasted of, or felt hard like, metal. Just then, Meg grabbed him by the hair, and hauled him back, and the nun on the rack disappeared.

“Good job, Dean-o. You got rid of all that nasty mesh. Of course, it’ll just be put right back on, now that she’s back with the demons in charge of her torture - they lack imagination, and they think it’s funny to put a chastity belt on a nun - but hey, at least you gave her a couple of minutes that were pain free, and maybe you gave her a little pleasure, too. Not that she’d thank you for it, but still. You did really well, Dean. Good boy. Be proud of raping that nun so well.” Meg patted his head condescendingly.

Dean cleared his throat and spat, trying to clear his mouth of that foul metallic taste, but made no comment. 

“Would you like a drink of water, Dean? I’d say you’ve earned one.”

Dean nodded, keeping his eyes on the floor.

“Beg for it, Dean.” Meg grinned.

_ Meg  _

“Please, may I have a drink of water?” Dean managed to get the words out, though he felt like he was choking on them.

Meg held a flask to his lips and tilted it so the fluid inside dribbled down into his mouth. Clear, clean water - and Dean thought he’d never tasted anything quite so good.

Meg patted his head gently. “We’ve only got a moment, Dean. Alastair slipped out of the room to get something, but he’ll be back. Look, I can’t get you out, but I can deliver messages topside, if you want. Anything you want me to tell Sam? Someone else?”

Dean looked up at her face, startled. “Why? Why would you risk that, for me? You hate me.”

“Aw, Dean. Hate? Nah. You did your job, I did my job. That’s all. So, messages? Think quickly.”

Dean shook his head, and dropped his eyes to the floor again. He didn’t trust Meg to actually deliver any message he might think of to anyone he’d want to get a message to, and he didn’t want to give anyone topside false hope for his safety. Especially not Sammy. Better than he just be forgotten.

“Last chance, Dean-o. No? Nothing? All right, then.” Meg grinned. “Smart boy. I wasn’t going to actually deliver any message anyway, just wanted to see what you’d say.”

Dean rolled his eyes, just a little, hidden from Meg’s view. “At least I got a drink of water out of you.”

Meg laughed. “True. You did.”

Dean couldn’t help smirking.

And then, suddenly, he was back on Alastair’s rack. He could hear Alastair and Meg talking, though he couldn’t make out what either of them said. They walked back over toward him.

“So, Dean, what did you think of Meg’s audition? On a scale of one to ten, what would you give her? Think about the pain she caused you, that nun, how creative her torments were, etc. It’s very important that I have accurate information as I make up my mind about my successor, after all.” Alastair smiled, and Dean’s flesh crawled.

“Yeah, Dean, let’s hear it, I want to know what you thought. How’d I do?” Meg asked.

Dean stayed silent, his eyes down.

“The peanut gallery is silent? What a change,” Meg mocked.

“Well, I guess I’ll have to evaluate you, then, Meg. Dean, feel free to chime in here,” Alastair said, expansively. “For the work with electricity, I’d give you a solid nine, Meg. Perhaps you could have raised the voltage a bit while Dean was ‘dancing’ for you, but I liked that you used the increase as a threat to get him to ‘dance’ faster, so that balances it out a bit. 

“For referencing the brother, and threatening him, though, I’d only give you a two. It’s not a very effective threat when you have to ask first if the brother is even within your grasp - a question, you’ll notice, I never answered. 

“But the nun! Now, that, Meg, that was truly inspired work. Causing her physical pain which only Dean could relieve, then causing her emotional pain by having him relieve it, which, in turn, caused  _ him _ emotional pain… delicious! And then the coup de grace - it was all for naught, because the chastity belt will just be put right back on! Solid work, Meg. I rate that part of the audition a ten. But I have to knock you down a half point for allowing him a drink of water afterward. I’ve been keeping poor Dean a bit dehydrated on purpose, you see. So, nine point five from the Romanian judge. 

“And then, the final bit, to allow him to think that you might be willing to carry a message topside, which served a few purposes - one, to give him hope of an ally; two, to make him think about those he cares about; and three, when he realized you couldn’t be trusted, to dash his tiny hopes. That, I rate a six. He didn’t really believe you. If you’d slotted it in earlier, he might’ve. 

“So, let me see. Nine plus two plus nine point five plus six is twenty-six point five, divided by four is six point six two five. Hmmm. Not a stellar average, despite two very high marks. Disappointing.”

“I did believe her.”

“What was that, Dean?” Alastair asked, as if he couldn’t believe Dean had dared to speak.

“I said, I did believe her. About the messages. I didn’t ask her to send one, but it wasn’t because I didn’t believe her that she’d be willing.”

“Hmmm. Well, then. Perhaps I should reconsider that part of the score. Since Dean says he did believe you, Meg, I’ll revise that part of the score upward to… let’s say an eight. Overall score of twenty-eight point five, divided by four is seven point one two five. Unless, Dean, you have something else you’d like to contribute, here?”

Dean kept his eyes down, and shook his head.

“No? Well then. Seven point one two five, Meg. Not too shabby.”

“Word is you gave the first candidate a reward without announcing points,” Meg pointed out.

“Consolation prize. He was a smoke demon, not much he could do, really, but he wasn’t cut out to be my successor. I gave him a reward just so he wouldn’t be bitching about me in the Pit to the other demons. Your reward is your score, and as it’s a pretty darn good one, I’d advise you to take it, and be glad of it. And be grateful to Dean here, for speaking up and getting me to increase it.”

“Yeah. I am. Grateful, indeed. Thanks, Dean.” Meg’s sarcasm was obvious, but Dean kept his eyes down.

“Well, guess I’m off then. Things to do, people to fuck over. I’ll hear from you?” Meg asked Alastair.

“Indeed.” 

Meg nodded, then vanished.

“Now then, Dean. I think I have just enough time before the next candidate to work on you myself for a bit. Have you been missing me?”

“Not a bit.” Dean regretted saying it as soon as the words were out of his mouth, but Alastair just chortled a bit.

“Well, Meg did keep you fairly busy for a while there. Well, let’s see what I can do.” He picked up his favorite scalpel. “Today, let’s see how many cuts I can make before you start to bleed. Tell you what - if I get to 100 and you haven’t bled yet, I’ll let you get some sleep tonight. Would you like that, Dean?”

Dean didn’t respond, afraid that if he did, either way, Alastair would take it back.

“When I ask a question, Dean, I’d appreciate an answer. But no matter. Let’s get started, shall we?” And with that, he began to slice into Dean’s skin. 

Dean tried not to make a sound, tried not to twist in his bindings, but it was hard to try not to avoid the pain. By the tenth cut, he was whimpering softly; by the thirtieth, he was crying out; by the sixtieth, he was screaming.

He tried to escape into his head. 

_ Sammy, I hope you’re not down here. If you are, it’s my fault; I’m so sorry. _

But his thoughts offered no real escape, and instead of taking him away from the pain, they only made the tears start to fall. Dean tried to sniffle them back, but it didn’t work. The pain was just too much, and soon, he was freely weeping.

_ I’m so tired. I hope I’m not bleeding yet. I want so badly to sleep. _

“Ah, that’s the one hundredth cut, and still no blood. Well, Dean, good news. Sleep for you tonight.”

Dean sagged on the rack in relief.

“But we’re not there, yet. It’s only mid-afternoon, and I’ve got a third candidate lined up. Shall we call them in, Dean?”

Alastair snapped his fingers, and Dean’s skin reattached itself everywhere he’d just been slicing it off. “Can’t have you damaged already when a candidate starts in, now, can we?” 

***

**Notes for the Chapter:**

> Please comment! I'd really like to know what people think!


	6. Third Candidate's a Bust; Dean Makes a Friend

**Summary for the Chapter:**

> The third candidate for the position of Alastair's apprentice - Ruby - comes in, but lacks the references and has a conflict of interest - and therefore removes herself from competition. Alastair decides to let Dean have the promised sleep, but Dean is so untrusting of being able to relax that even just sleeping becomes a torment. When Dean wakes, the succubus is back, but this time, she decides to give Dean a break.

Dean hung from the rack, face still covered in tears, though his eyes were now dry. He was so tired. Maybe this third candidate would be incompetent and quick; then he could sleep.

“Hello, Dean.” 

Dean looked up at that voice. 

_No. No, please, it can’t be. Not her._

But there she was. Ruby. Sam’s demon “friend” who had lied to them, told Sam that she could get Dean out of his crossroads deal to save Sam, without Sam having to die again. 

_Ruby_

_Well, Lilith_ **_did_ ** _say she’d sent Ruby back to Hell_. 

“Ruby.” Dean acknowledged her presence so he couldn’t be accused of being rude to her.

“Ruby, I’m going to pop out for just a second, I need some things from your application that I left in another room. You two go ahead and get reacquainted, why don’t you?” Alastair left the room.

“Dean, I’m sor….”

“Save it. Just… tell me. Is Sammy safe? Do you know?” Dean asked.

“I… I don’t know. You probably know more than I do. Lilith blasted me to the far reaches of Hell. It took me a couple of months to work my way back up this far, I haven’t dared go topside yet.” 

“Last I saw, Lilith was wearing your meat suit, and she was about to blast Sammy, but I bled out on the floor beneath her hellhound before I could see what happened.”

“Sounds like her.”

Alastair came back in, then. “Ruby, a word, please?”

Ruby crossed the room to Alastair’s side. “Yes?”

“Your references are… lacking. You worked closely with Lilith, but there’s nothing here from her.”

“We had a… disagreement with regard to my most recent assignment. With all due respect, Alastair, I can’t really discuss it in front of the subject. Can we go into the next room?”

“Ah. Of course. After you.” Alastair gestured to the door, and Ruby exited the room, with him behind her. 

Dean strained to try to hear what was being said, his mind whirring with activity.

 _Lilith blasted Ruby and refused to give her a reference; she had to work her way back up from the bottom of the Pit; they had a disagreement over her ‘last assignment’ - because she’d helped Sammy, helped us. Even though she lied to me, she_ **_did_ ** _help._

Alastair stepped back into the room. “Well, Dean, it appears that Candidate Number Three has a conflict of interest, and has removed herself from the competition.”

Dean breathed a shallow sigh of relief. 

“So, I thought I’d give you a bit of a treat.”

_Oh, no. No…. This can’t be good._

Alastair snapped his fingers, and Dean was in what he’d come to think of as “the bedroom” - the room with the bed where the succubus sucked him to the point of pain, usually - but instead of the succubus, the room was empty except for Dean. Dean was unrestrained, whole, not in pain - for once - and alone. 

And terrified. 

But the human mind can only take so much stress before it shuts down and stops feeling it, and Dean had reached that point. He sank down onto the edge of the soft bed, and felt his muscles relaxing. He tried to stay alert, certain something awful was about to happen, but couldn’t manage it. He laid back, sank into the comfortable mattress, and his mind went… away. Without meaning to, he slept, deep, and dreamless, his mind seeking the rest it had been craving since he’d arrived in Hell.

If he were conscious and thinking actively, Dean would’ve been impressed. Now, even being just left alone to rest was a form of torture.

***

Dean awoke slowly, comfortable and rested. So comfortable, in fact, that he didn’t remember where he was, at first.

Then, he opened his eyes, and saw the succubus sitting on the end of the bed.

_Oh, no._

“Good morning, Dean Winchester,” she said, in her lightly accented voice. “Alastair told me to let you sleep until you woke up. I gather he felt you were in need of some rest. And now, I make you feel good, yes?”

“Please, don’t.” Dean almost whimpered.

“Ah, you don’t like the oversensitivity. I don’t _have_ to do that, you know. I _can_ just make it good for you. How about you just relax, and let me, eh? I think, too, that perhaps we have all been just a bit too harsh with you lately.”

Dean shook his head and tried to shrink back from her touch. She just smiled sadly down at him. 

“So afraid. I am truly sorry that it has come to that, Dean Winchester. I enjoy you. I’d like for you to enjoy me, too. _Relax_. Let it be good for you.”

She snapped her fingers, and Dean was bound to the bed, spread-eagle, as he always was with her. 

“I have to say, this isn’t exactly inspiring confidence that you’re going to be different, here,” he told her.

She laughed quietly. “I suppose not. But you will see.”

She moved to kneel between his legs. Despite his dread, Dean’s cock was already hardening, as it always did when she was near. Apart from the magic attraction of a succubus in general, she was exactly Dean's type (except for the horns) - raven hair, blue eyes, pale skin, slender, with breasts that were a bit more than a handful.

She stroked him gently with one finger, and he shivered. She leaned forward and kissed him gently, then moved slowly down his torso, kissing and lightly nibbling his skin, all the while continuing the light touches on his cock, stroking him to full hardness by the time her mouth reached his groin. She looked up and smiled softly at him.

“See? Feels good, yes?”

Dean nodded, breathless. It _did_ feel good. But it _always_ started out that way, with her. It felt good… until it didn’t. Until he was suddenly screaming from the pain of oversensitivity. So, maybe he was untrusting, but he couldn’t make himself relax and believe that she wouldn’t hurt him.

The succubus’ hands caressed his thighs soothingly, as she bent and took him gently into her mouth, moving just her lips along his length. Dean moaned softly, his eyes closing involuntarily as she began to suckle slowly, carefully, and, this time, not just at the tip, but along his whole cock, her lips sliding along him, moving over his flesh, then back up to the tip, and… then she was swallowing him down, and he cried out, gasping at the pure pleasure of it, no pain involved.

She continued to work him softly, tenderly. Dean trembled, not from fear but from ecstasy unlaced with pain. This was just good, so _very_ good, and while he still didn’t quite trust it, he couldn’t help but relax into it, give in to it. He began to move his hips helplessly, thrusting gently up into her mouth, and she smiled around his dick. 

“Please….” Dean whispered. 

“For what are you asking, Dean Winchester?” The succubus slid her lips off of him and sat up to ask the question, and she smiled softly at him.

“What’s your name?” Dean asked.

She looked surprised, but answered him. “My name is Elena.”

“It didn’t feel right, somehow, to do these things with you, and not know your name.”

“Ah. You are a gentleman, Dean Winchester.” 

_Elena the Succubus_

“Am I?” Dean huffed out a quiet laugh. “If you say so.”

“I do. So, are you trusting me a bit more, now? May I continue?”

“Do you want to?” Dean asked. “I mean, really, is this what _you_ want?”

“I feed from your emotions, from what you feel. Is good meal, to give you pain. But is _better_ meal to make you feel _good_. From time to time, I do not mind relaxing the rules. You get to feel something pleasant, and I get fed well, yes?” Elena winked.

A bit startled by that, Dean laughed again. “I don’t mind, if you don’t.”

Elena grinned. “Then I shall continue, yes?”

Dean nodded. “Thank you, Elena.”

“You are welcome, Dean Winchester. Just remember, I cannot do this very often. Try not to think too harshly of me when I must go the _other_ way, yes?” She didn’t wait for an answer, simply bent her head and took him into her mouth again, reaching between his legs with one hand to fondle his balls.

It didn’t take long, and Dean arched, gasping, as he found his release.

***

**Notes for the Chapter:**

> Please, please comment. I *really* want to know what people think of this story! Thanks for reading!


	7. Something Old, Something New

**Summary for the Chapter:**

> Dean is bound in place on his knees and forced to remain perfectly still while being swarmed with angry bees and whipped by the next candidate for the position of Alastair's apprentice. Dean is then put in sensory deprivation, but can still feel the beestings and whip welts. The next day, Alastair removes all of his skin, which, when he removes the bits with raised bruises, is almost a relief, at the start. Dean is put back together, and a barbarian demon named Roland tears him literally limb from limb, dislocating each joint along the way. Dean is put back together again, and told that from time to time he will serve as a staff member at Hell's new brothel, where demons are rewarded for good service to Hell with good service from souls such as Dean. Dean meets the brothel's manager, Anandas, who promises to be a "fair employer", and explains the rules. Dean also meets Anandas' pet wolf, Marquis "Mark" de Loup.

The next candidate bound Dean in place on his knees, though his hands were free. He told Dean to remain perfectly still, not to move, no matter what, then caused a swarm of angry bees to cover him. Within moments, Dean’s skin was covered with raised dark red welts from the stings, as well as from the whip the candidate used to slash at him through the insects. 

Dean kept his position, and kept his eyes down, his hands still; he succeeded in not trying to slap the bugs away. He just managed to keep his mouth shut, keeping his lips together, not wanting bees to get into his mouth, but he couldn’t stop himself from whimpering. 

Dean had hated bugs of all kinds, but in particular bees, ever since a case about a Native American curse that he and Sam had taken on a few years before, where they’d ended up stuck in an attic with a few other people and literally thousands of bees had attacked them through termite holes in the roof. 

He didn’t know if the candidate had been aware of his feelings, but Dean assumed that it made for a great audition piece, as Dean was truly terrified. Indeed, Alastair gave the candidate high marks. 

When Dean went back to sensory deprivation this time, it was with the exception that he could still feel each and every one of the hundreds of bee stings and welts of the whip that covered every inch of his skin.

***

Dean came out of sensory deprivation slowly; when he tried to kneel, he couldn’t - he was already bound to the rack and simply hadn’t realized it at first. The bee stings and whip welts were still an agony, and now, here was Alastair, stepping up with his scalpel.

“Good morning, Dean. I realized that I had forgotten to ask last night; did you want to accept my offer, after the most recent candidate’s audition piece, or shall we proceed?”

Dean's reply came slowly and quietly - but with no less intensity than the first time: _“Sc...rew…._ _You….”_

“Oh, Dean. Such originality,” Alastair said, dryly. “But fine, we’ll record the ‘no’ for yesterday and begin anew today. Well, not quite anew, since you still have all these lovely raised bruises, but we’ll call it close enough, since I’m just going to filet off all of your skin, anyway.” With that, Alastair started slicing; today, Dean experienced it as almost a relief at first, as the welts were removed, but he knew that feeling wouldn’t last long. He was correct; Alastair had him screaming soon enough.

As Alastair removed the very last piece of skin from Dean’s flesh, he snapped his fingers, and Dean was whole again.

“I don’t really have time to spend on taking you completely apart today, so just removing the skin’ll have to do. That’s my favorite part, anyway. And now, I’m going to turn you over to Roland.”

Roland was a very large, very old demon, who might very well not have been actually human, but older. He certainly fit Dean’s idea of what a ‘caveman’ would have looked like. 

Roland liked to slowly dismember people with his bare hands. He started with Dean’s fingers, and worked his way up, twisting to dislocate, then tearing free, each joint. When he had removed each of Dean’s arms completely, he’d move to the feet and start again, moving upward until the hip joints had been snapped. Then he’d rip free Dean’s cock, then his balls. There being left then only Dean’s torso and head, the head was next, and then it was over. Roland left Dean in a pile of sentient, conscious, pieces and parts on the floor, and lumbered off to his next victim, somewhere else.

***

Alastair came in and snapped his fingers. Dean was whole again, and bound again to the rack. He tried to breathe slowly, to not let Alastair see how much Roland’s slow work had affected him.

“Well, Dean, something new for you; I wouldn’t want you to get _bored_. As you may be aware, Lucifer is technically the ruler of Hell, but he’s, shall we say, _indisposed_ , being that his Father long ago locked him in the Cage, from which he cannot communicate with us, his loyal subjects. However, before he was locked away, he had the foresight to form a committee of certain high-ranking demons to make decisions in the event that he was unable to do so; as Grand Inquisitor, I sit on that committee, along with the Princes of Hell, Lilith the First Demon, who I believe you’ve met, and a few others. Now, there are always demons who have earned rewards, and hardly ever sufficient rewards to give out. So, the committee has decided that we should open our own little brothel, Hell’s Whorehouse. Deserving demons will receive tokens that can be spent on various goods and services to be made available at the brothel. 

“But that leaves us needing staff members for the brothel. So, those of us on the committee with our own, shall we say, pets? have volunteered to help with staffing. So, from time to time, Dean, you’ll be on staff at Hell’s Whorehouse. That might mean you serve drinks; it might mean you get gang-raped. It all depends on the needs of the brothel, as determined by its manager, Andras, and its customers. Very few things that a customer - a demon being rewarded for good service to Hell - desires will be denied to it. I really would like to promise that you won’t be harmed, but, of course, you _will_. It’s a reward for others; it’s a new torture for you. You start tonight.” 

Alastair snapped his fingers again, and Dean found himself kneeling in a small room.

***

Dean glanced up briefly and realized he was kneeling in front of a desk, and that there was a demon on the other side of the desk, who appeared to be looking him up and down appraisingly. The demon had a head shaped like an owl’s, with strips of skin interspersed with strips that were feather-covered, large oval eyes, and a hooked beak, but the rest of his body was human-looking, and his speech was clear and crisp. Behind the desk, and behind the demon’s chair, there was what appeared to be a very large black wolf, laying on a very large bean-bag chair, which was clearly the wolf’s bed.

“You’d be Alastair’s pet, then? Dean, right?” the demon asked.

Dean nodded. “Yes, Sir.”

“I suppose you’ll do. My name’s Anandas. My friends call me Andy, but you can call me ‘Sir,’ that’s fine. We’re not friends; or, at least, not yet.” Anandas grinned. “The wolf’s mine, or at least, he consents to hanging around with me on a fairly consistent basis; his name’s Marquis de Loup, but you can call him ‘Mark.’ He’ll answer to it. Ignore the teeth. He’ll probably want to make friends with you, he’s a big dork.” The demon clicked his beak softly at his pet.

Anandas Mark the Wolf 

“Look, Dean, I’m going to start you out slow, not as a favor to you, particularly, but because there’s a learning curve to everything. If I drop you in at the deep end of the pool right away, you might learn faster, but you might also make mistakes that piss off the customers, and they’re here to be rewarded. So, it’s not for your benefit, see? It’s for _theirs_. And for my own sake; I don’t want complainants to go above my head. I used to rule over 30 legions of Hell; I was a Grand Marquise of Hell, just below the Princes; I rode Mark here into battle in the old days. But sometime in the thirteenth or fourteenth century A.D. - I forget now, exactly when it was - I had a falling out with Lilith. I had to work my way back up from the bottom of the Pit for this position, and I intend to keep it. So, it’s in my own best interests to train up the staff well, and make sure that they understand their place, and how to best please the customers. You following me, here, Dean?”

Dean nodded again. “Yes, Sir.”

“Good boy. Now, technically, I’m allowed to tell you to do anything I want you to do, for as long as I want you to do it, without a break, without rest, without time to get a drink or food or go to the bathroom, because, technically, you don’t need to do any of that. Resting, eating, drinking, all non-essential when all you are is a soul without a real body. But because you’re still projecting a body rather clearly, and Alastair doesn’t really want you taken down to nothing but smoke - or at least, not right away - you’re still prone to the _illusion_ of needing those things, and I’m inclined to let you have them. A bit of a rest now and then will make you more responsive to the customers’ needs and better able to satisfy them. So, you’ll be worked, and worked hard, but you’ll be given regular breaks with time to rest and given something to sip on, at a minimum. I’m a fair employer, Dean. Do your job well, I’ll treat you as well as I can within the confines of the assignment. Act out, and you’ll be strapped down and raped, or whatever other horrible perversions the customers decide they want you for. You ever worked as a bartender, Dean?”

“Yes, Sir.”

“Excellent. That’s where you’ll start out, then. Manning the bar in the main lounge. I’ve been needing someone who knows how to pour a decent drink. We don’t water’em down. If a customer offers to buy _you_ a drink, you accept it, but you _don’t_ knock it back. Take the token, fake a shot pulled from a bottle that’s been set aside and marked for the purpose. Got it?”

“Yes, Sir.”

“Good. The more reward tokens you can pull in for things these idjits want to do _for_ you, like buying you a drink, the better. Those tokens go in a separate box, below the cash box, and I’ll empty it four times per shift, when I come to relieve you. Each shift lasts sixteen hours; you get a ten-minute break every four hours, when I come out to the bar to relieve you, and not before. We clear?”

“Yes, Sir.”

Anandas nodded. “Good. Stand up.”

Dean rose to his feet. Anandas came around the desk and slipped a heavy leather collar around Dean’s neck. “Marks you as the brothel’s property; you have to wear it when you’re on the brothel’s premises. Come to me at the start and end of every shift and I’ll put it on and remove it for you. Give me your hands.”

Dean raised his hands obediently, and the demon slipped plain leather bands around each wrist, as well. “Those will tell the customers two things - one, that you’re not to be taken out from behind the bar without permission from management, and two, that management will back your decision not to serve them. If someone’s getting rowdy and threatening to do damage - to the brothel, its property, its staff - including you - its other customers, or to themselves, doesn’t matter - you can cut them off, Dean. And I _will_ back you on that. But you’d best be right about their intent, hear? There are cameras in the lounge, and footage will be reviewed. Clear?”

“Yes, Sir. I understand.”

“Any questions, Dean?”

“Are the wristbands and collar _all_ that I’m to wear? Or do I get any kind of a uniform beyond that?” Dean asked, mildly, keeping his eyes down.

“Good thought. Look, Dean, you don’t have to be afraid to ask questions, or make suggestions, okay? As long as we’re in this office, you can speak freely to me, and I’m not going to punish you for it. Just not in front of the higher-ups, and not in front of the customers. Got it?”

Dean nodded. “Yes, Sir.”

“All right, then.” Anandas snapped his fingers, and Dean was wearing a tight-fitting pair of hot pink short-shorts with a black stretch waistband; they didn’t cover much, but enough that Dean was ‘decent’, as long as he didn’t bend over from the waist. Dean blushed a little, but it was better than having to serve completely naked.

***

**Notes for the Chapter:**

> Please comment! Comments are life! Thank you!


	8. Missing Ingredients

**Summary for the Chapter:**

> Dean works his first four hours and it goes well; he gets relieved by Anandas and takes his first break. Anandas gently chides him for not having earned any tokens for the box by having someone offer to buy him a drink and tells him to step up his flirting game. A customer, Abraxas, wants a drink for which Dean lacks the ingredients; Dean offers a substitution, but Abraxas demands to see the manager. Anandas and Abraxas come to a compromise - Anandas will order the ingredients for Abraxas' drink, and, in restitution for the lack of them this time, gives Dean to Abraxas to do as he likes. Anandas removes the wristband that denies customers the ability to remove Dean from behind the bar without management's permission from Dean's wrist, and Abraxas hauls Dean off to one of the brothel's sex work rooms, purposefully tripping Dean on the way into the room so he falls on his hands onto the bed.

Mark had followed Dean out to the bar, and was now sleeping in a corner behind where Dean walked along the rubber mat on the floor to serve drinks, out of the way. Dean was almost having a good time, actually. Pouring drinks wasn’t hard, and while his naked feet were a little sore and his extremities were a little cold from being bare, all in all, this duty wasn’t bad. It was certainly better than being bound to a rack and having Alastair cutting into him. 

After four hours, Anandas came out of the back office and surveyed the lounge, then nodded, satisfied. The customers looked happy and relaxed, and Dean seemed to have the bar well in hand.

Anandas came around the end of the bar and told Dean, “You’re on break. If you go out the other end of the bar and turn left down the hall, about three or four doors down on the right, you’ll see a door marked “staff room.” You can go in there, get some water, and sit or lie down for a few. Be back out here in ten.”

Dean nodded, and left the bar, following Anandas’ instructions. He found the staff room with no difficulty. It was a fairly plain room, with a few chairs at tables, a couple of couches up against the wall, and a mini-fridge with bottled water. At the moment, it was empty, except for him. There was a marker on a string hanging from the fridge door, and Dean could see that some of the partially-emptied bottles had letters written on the label, apparently the initials of whoever had started drinking that particular bottle. Dean figured that bottled water was what Anandas intended for him to drink, since there was no sink, hose, tap, or other source of water in the room that he could see, so he took a bottle and sipped it, slowly. He was dehydrated, but knew that too much, too fast, would make him sick, and he had to be back out front in a few minutes. 

Dean laid down on one of the couches, and closed his eyes to rest them for a moment. He didn’t let himself relax too much, not wanting to fall asleep on the job, but it felt really good to be off his feet for a bit. No one was torturing him at the moment, this was a job he could handle, and he got to rest a little now and then; the collar was a little tight, but Dean wasn’t complaining.

After a couple of minutes, he swung himself up to a sitting position, and leaned back against the back of the couch, sipping a little more water. He stood slowly, used the marker to put his initials on the bottle’s label, and put it back in the fridge, then headed back out to the bar. It hadn’t been a long break, but he was grateful for whatever he was given.

Anandas looked up as Dean stepped back behind the bar, and nodded to him. “Good job, right on time. I checked the box, no tokens. No one offered to buy you a drink?”

Dean shook his head. “No, Sir.”

“Well, step up your flirting game, then. Rope’em in, hear? Now, it looks like the register’s doing all right, and I’ve been watching the cams off and on, you’ve been doing a brisk business, and you’re handling it well. And that’s good, but we want ‘em spending those tokens in as many ways as possible that don’t actually involve moving inventory, so get ‘em interested and on the hook.” Anandas glanced at Mark; the wolf had been sound asleep, but now was sniffing at Dean’s hand with interest. “See, I said he’d want to make friends with you.”

_ Dean and Mark behind the bar _

“Can I pet him? Will he let me?” Dean asked.

“Yeah, go for it. He’s not domesticated, by any means, but if he knows you won’t hurt him, and you’re gentle, he likes being petted and scratched from time to time. He won’t bite a friend. Go ahead.”

A customer came up and Anandas served them while Dean scratched Mark’s ears gently. Mark’s tongue lolled out, and Dean swore his eyes crossed with pleasure just for a second. Then Mark bumped into Dean’s leg with gentle affection, and turned back to his little area to lay down and go back to sleep. Dean chuckled softly.

“All right, Dean, bar’s yours. See you in four hours,” Anandas told him, then headed back to the office. 

Dean wiped down the bar with a cloth, then served a customer their requested beer. He was just putting their token in the register, when one of what Dean had silently dubbed ‘the loudmouths’ stepped up to the bar.

“Hey, you. Bartender. I need a bottle of Jager and a coupla cans of Red Bull. I wanna make Jager Bombs.” The demon didn’t look intoxicated, yet, Dean thought.

“Sorry, buddy. No Red Bull. No Jager, either. If you see it up here behind me, you can have it, but that’s all we’ve got,” Dean told him.

“I ain’t yer buddy. I’ve had my mouth set on a Jager Bombs ever since I got this stupid token, and now you’re gonna have the nerve to tell me you don’t have the makin’s? Who does your ordering, man? You? ‘Cause I bet I could get you to remember Red Bull and Jager for your next bar order.”

“I don’t do the ordering, Sir. Look, I’ve got scotch, creme de cacao, and ginger ale; I can make you a Bomb Dot Com,” Dean suggested.

“You don’t hear very well. I want Jager Bombs. And if I can’t get one, it’s your problem.”

Dean sighed. “Sir, I don’t have the ingredients for Jager Bombs. I do have the ingredients for a Bomb Dot Com, which is a good substitute. If you don’t want a Bomb Dot Com, then I don’t know what else to say. I don’t do the ordering, I just pour the drinks.”

The demon scowled. “Do you know who I am?”

“No, Sir, I can’t say that I do.” Dean smiled.

“My name’s Abraxas, boy. You’d do well to remember it.”

Dean nodded. “Yes, Sir. Now, would you like a Bomb Dot Com? Or can I pour you just a straight shot of something? Be a shame to waste the trip.”

“I ain’t wasting a token. Who’s the manager of this joint?”

“The manager’s name is Anandas, Sir.”

“Oh, that pansy owl. No wonder. If he’s doing the ordering, this bar’ll never be stocked proper. Get him. I wanna have a little chat with ol’ Andy.”

“I’ll see if I can get him, Sir.” Dean looked around, decided the rest of the lounge was quiet enough that he could take a second away from the bar, and ducked out the end of the bar near the office. He knocked on the office door, conscious that Abraxas had followed him.

Anandas came to the door and opened it. “What’s the problem, Dean?”

“We have a patron who is complaining about our lack of ingredients to make Jager Bombs. I offered to make him a Bomb Dot Com, instead, but he asked to speak with you, Sir.”

Anandas’ eyes twinkled. “Well, send him in. I’m happy to speak with customers. And then get your ass back behind the bar, Dean.”

“Yes, Sir. Abraxas, Sir? Anandas will see you in the office now.” Dean gestured to the door, and waited for Abraxas to pass him before scooting back behind the bar. No one else in the lounge had moved. Dean sighed in relief.

Dean wiped down the bar again, then served three more customers. Then Anandas and Abraxas came out of the office, and Anandas called Dean over to that end of the bar.

“Well, Dean, Abraxas and I have settled our little dispute. I’m going to order the ingredients for Jager Bombs for him, so you’ll be able to serve him in the future. And for today, to make up for the lack, I’ve agreed that Abraxas should be given restitution. Give me your left hand, Dean.”

Dean got an uneasy feeling in the pit of his stomach as he raised his left hand and offered it to Anandas obediently. Anandas removed the left wristband from Dean’s wrist.

“This is the wristband that says customers can’t make you come out from behind the bar without management’s permission, Dean. By removing it, I’m giving Abraxas permission.” Anandas’ eyes glittered a little, as he watched Dean’s face.

“Sir…? Permission to do...what?” Dean asked, realization slowly dawning.

“Whatever I want, bitch.” Abraxas grabbed Dean’s wrist, and pulled Dean along in his wake, heedless of Dean’s terrified resistance, as he stalked off down the hall toward the brothel’s rooms set aside for sex work.

Abraxas stopped in front of a door. Next to the door was a green placard, indicating that the room was available. Abraxas turned it over with his free hand to reveal a red placard, indicating that the room was taken. He opened the door with the same hand, keeping his other hand locked around Dean’s wrist. He pulled Dean in front of him and thrust Dean into the room with a shove that had Dean staggering forward and falling onto the bed on his hands.

“That’s perfect, slut, stay just like that.” Abraxas entered the room and locked the door behind him.

Dean didn’t dare to do more than look back over his shoulder, then back down at his hands. He swallowed hard. 

“Before I’m through with you, you’ll _beg_ me to fuck you.” 

***

**Notes for the Chapter:**

> Please, please comment! :D


	9. Come for the Betrayal; Stay for the Rape

**Summary for the Chapter:**

> Abraxas whips Dean until Dean is ready to do anything to get some relief from the pain. He makes Dean beg to be fucked. He partially heals Dean, saying he wants to believe that Dean wants to be fucked, not just relief from pain. Dean begs again, and Abraxas rapes him. Before Abraxas can finish, Anandas interrupts, as it's time for Dean's break. Abraxas leaves, and Anandas heals Dean and apologizes.

Abraxas stopped in front of a door. Next to the door was a green placard, indicating that the room was available. Abraxas turned it over with his free hand to reveal a red placard, indicating that the room was taken. He opened the door with the same hand, keeping his other hand locked around Dean’s wrist. He pulled Dean in front of him and thrust Dean into the room with a shove that had Dean staggering forward and falling onto the bed on his hands.

“That’s perfect, slut, stay just like that.” Abraxas entered the room and locked the door behind him.

Dean didn’t dare to do more than look back over his shoulder, then back down at his hands. He swallowed hard. 

“Before I’m through with you, you’ll beg me to fuck you.” 

Dean closed his eyes, trembling. He didn’t doubt that Abraxas could, and would, make him do just that.

Abraxas snapped his fingers, and Dean’s shorts were gone. Nude again, but for the collar and remaining wristband.

“Dammit, I wanted the collar and wristband gone, too. Take ‘em off, slut.”

“I can’t, Sir,” Dean explained softly. “As in, I literally, physically, cannot remove them myself. Anandas has to take them off of me at the end of my shift. They mark me as property of the brothel during my time here.”

“Hmmph. Fine. Keep’em then. Maybe I’ll even get some use out of’em.” There was a tall chest with drawers, and a cabinet with two doors along one wall of the room. Abraxas stepped over to the chest, opened and rummaged around in a drawer for a moment, then stepped up right behind Dean. Dean felt fingers between the collar and his neck. Then Abraxas did something, and Dean’s neck jerked backward, hard enough that, had he actually still been alive, his spinal cord would have snapped. “Heh. That’ll work.” 

Dean glanced up as Abraxas reached over to the wall, and saw that there was a long leather leash that the demon was attaching to a hook set into the wall above the head of the bed; he realized the other end was connected to the collar and was the thing that Abraxas had yanked on. 

Abraxas finished hooking the leash’s far end in place, then started winding the leash around two other, slightly lower, hooks, shortening the leash and drawing Dean closer and closer to the wall. Dean had to rise from the bed to keep from choking before the demon stopped.

“Kneel on the bed, slut.”

Dean obeyed promptly. He didn’t want to do anything to piss the demon off more than he already was. His knees were just below the pillow, and he was leaning forward slightly, hoping that Abraxas wouldn’t consider that slight deviation from proper form a punishable offense, given that Dean literally couldn’t straighten further. He kept his eyes down, his knees wide apart, his ankles crossed, his palms open, the back of his hands resting lightly on his thighs - except for the leaning, in perfect form.

“Is that as far apart as you can get those knees, bitch? Widen’em, let’s see you try.”

Dean obediently tried to spread his knees further apart, and succeeded by about a quarter inch, but that caused him to have to lean forward a bit more.

Abraxas chuckled. He pushed Dean’s head down onto the pillow. “Raise up your ass. Let’s have you head down, ass up. Otherwise, don’t move. You’re spread open perfectly.”

Dean pushed his hips up as far as he could with his knees spread as far as they were. He laced his fingers together, and set his hands on the back of his neck.

“Yeah, just like that. You just stay right there. Perfect.”

Dean couldn’t see what Abraxas was doing - the pillow beneath his face was effectively blindfolding him, and he couldn’t peek out past it without moving - but he could hear the demon stepping away, a door opening - presumably to the cabinet - and closing again, and then the demon stepping back toward the bed.

And then he heard a swish and a crack, and a cry.

A second later, he realized the cry had been his own, as Abraxas had opened a wound diagonally across his back with the whip the demon had apparently just procured from the cabinet.

Another swish, crack, gasping cry.

Another.

Another.

Dean was sobbing for breath and the pillow was soaked with his tears, and Abraxas wasn’t slowing down. Dean could feel sticky fluid - presumably his own blood - dripping down his sides from the slashes being cut into his back. After the tenth blow, Abraxas’ hands framed Dean’s head and he turned it to face him. 

“Beg me to fuck you, bitch. Beg me, and the whipping stops.”

“P-please,” Dean whimpered.

“What was that, slut? Please? Please _what_?”

“Please, Sir, please f-fuck me.”

“That’s better. But I don’t think you really mean it yet. You don’t seem very enthused. I want you to really _beg_ to be fucked, like you mean it, like you _want_ it, like you’d do _anything_ to have my cock in your ass. And I just don’t think you’re there yet.”

_Swish. Crack. Cry._

_Swish. Crack. Cry._

_Swish. Crack. Cry. Whimpering._

_Swish. Crack. Gasp for breath, sob._

_Swish. Crack. Cry._

“Good. Now, try again. Beg me to fuck you, and let’s have some ferver behind it, some gusto. Make me _believe_ it.”

“P-please, f-fuck me, please, I beg you, Sir, please,” Dean sobbed.

“Hmm. I just dunno.”

“ _Please Sir. Please,_ **_please_ ** _, please fuck me._ **_Please!_ ** _”_ Dean cried out.

“Hmm. Well, that’s a bit more believable. I believe that you want to be fucked more than you want to be whipped, at least, given the choice. But I want to believe that you _want_ to be fucked, whipping or no.”

Abraxas snapped his fingers, and Dean’s wounds were healed - or if they weren’t, he at least wasn’t in pain from them. Dean gasped.

“Now, try again, slut. Beg me to fuck you, and make me think you really want to be fucked.”

Dean swallowed hard. “Please, Sir. Please f-fuck me. I-I want it, want you. Please.”

Abraxas ran his hands over Dean’s ass and slipped a finger into his anus. Dean gasped, but made himself hold still for it. “This what you want, bitch? Something nice and hard pushing in and pulling out? Push back on my hand, show me how bad you want it, slut.”

“Y-yes, Sir. Please. Please fuck me. Please fuck my ass, Sir, _please_.” Dean sobbed again on the last word, as he obeyed the demon’s instructions, pumping his hips frantically.

“Mmm. That’s it, that’s what I want to see and hear.” The demon climbed up onto the bed behind Dean and knelt between Dean’s knees, pushing himself, hard and fast, into Dean with no further preparation. Dean screamed.

The pain was hideous, but, as usual in Hell, Dean could not escape into unconsciousness to avoid it. He felt as if he were on fire throughout his abdomen, as the demon’s cock speared him deep.

And when Abraxas chuckled and began to move, Dean sobbed in agony, trembling, desperately wishing for relief. 

And then came a knock on the door. Abraxas growled low in his throat, but pulled out and went to open it.

“Time’s up. Dean’s due for his break now.” Anandas smiled.

“But I’m not finished…” Abraxas started.

“Yes, you are, in fact. Dean is only on loan to the brothel. While he’s here, he’s property of the brothel, and I am responsible for him; but in fact, Dean’s soul is owned by Alastair. Thus, I intend to abide by all rules of the house for the proper treatment of our employees, and particularly when it comes to Dean-o, here. So, it’s time for Dean’s break, and therefore, you’re done, Abraxas.” Anandas held the door open for the other demon and gestured, politely, for him to leave.

Abraxas grumbled, but left the room.

Anandas shut the door behind him, and sighed.

Anandas came over and unhooked Dean. He framed Dean’s face with his hands, and looked deeply into Dean’s eyes.

“Yeah, I know, it hurts, but it’s repairable. I don’t have Alastair’s skill at putting people back together, I’m afraid, but I can mend you, Dean. Just give me a minute, all right?”

Dean nodded hesitantly, tears still streaming down his cheeks.

Anandas closed his eyes and whispered words Dean couldn’t make out. He reached down and slid his hand over Dean’s lower abdomen, and Dean gasped as the fire in his guts slowly faded away. Anandas slid a hand over Dean’s hip, and the rest of the aches and pains of the demon’s rape faded slowly, as well. Dean gasped for breath, the relief almost as agonizing as the pain had been, but eventually he relaxed, sagging onto the mattress.

“Go ahead and rest for a minute. When we walk out of here, and you will, Dean, you have to be fully upright and look as if nothing is wrong, understand? You’ll walk back out to the bar with me, I’ll put the wristband back on you, I’ll announce that it’s your break time, and you’ll go to the staff room for your ten minutes. Once you’re in the staff room, I don’t care if you fall to your knees and sob like a baby, but while you’re out in the public area, you will be calm, composed, and act as if there is nothing wrong, understand?” As Anandas spoke, he continued to heal Dean’s wounds, moving to the gashes in his back - which were, in fact, still wide open - and carefully splicing them back together.

Dean nodded slowly. 

“By the time your ten minutes are up, you should be fully healed. I won’t make you work the entirety of your last four hours, but you’ll have to do some of it, and you’ll have to act like it’s no big deal.”

“If I’m fully healed, I’ll be able to work, Sir.” Dean set his jaw.

“Take the time off, Dean. It’s an apology.”

“I don’t need it. What I need isn’t an apology, it’s honesty. I thought you said you’d be a fair boss. How fair was it to throw _me_ under the bus for an ordering mistake that _you_ made?”

“Hence the apology.” Anandas growled softly. "Look, I don’t generally own my mistakes, Dean; I don’t usually have to. Honestly, I don’t _have_ to here, either. I have control over your fate as long as you’re on the premises, as long as I heal you before sending you back. But I _am_ owning it, for a few reasons. You’re a good bartender, and I don’t want to have to replace you, either because you start to slack off because you feel I was unfair, or because Alastair doesn’t let you return because I let his property be damaged, healed or no. Plus, Mark likes you. The wolf’s a damn good judge of character. And honestly, I like you, too. And yeah, you’re right, it was a shit thing to do.

"But remember this, Dean. I didn’t _have_ to assign you to the bar. I could’ve assigned you to sex work - and what do you think sex work is, when you toss a pure soul like you to demons for use? It’s rape. I didn’t do that. So, you got it for one four-hour shift. You could have the same for twelve hours a day. So, take the apology, Dean.”

Dean considered, and nodded slowly. “Yeah. Okay.”

“All right, then. How are you feeling now? Able to go for that walk?”

Dean nodded again. “Yeah. I’m good.”

Anandas snapped his fingers and Dean’s shorts reappeared. He slipped the missing wristband back onto Dean’s arm. He helped Dean off the bed, and into a standing position, then waited for Dean to straighten up slowly. He nodded approval, then moved to the door and opened it.

“After you.”

***

**Notes for the Chapter:**

> Please comment!


	10. Did You Forget Something?

**Summary for the Chapter:**

> Dean settles into a routine. Most patrons, fearing Mark, who clearly favors Dean, leave Dean alone, but a few demons try to bully him, hoping to get him into enough trouble that Anandas will give Dean to them, as he gave Dean to Abraxas. After a few weeks, Alastair comes in and it's clear that Abraxas has talked with him about the incident. Alastair gives Dean a choice - he can serve in the brothel as a bartender, but work 20-hour shifts, then go straight to sensory deprivation until it's time to return, for five days in a row, then be with Alastair for two days of torture around the clock; or, he can serve to work as a bartender for an 8-hour shift, then as a whore for an 8-hour shift, then be tortured by Alastair or a demon of Alastair's choosing, for 8 hours; or, he can work as a whore for 24 hours on, then come to Alastair for 24 hours of torture. Dean chooses the first option, and the 20-hour shift begins immediately; having worked 2 hours already, he has 18 hours to go. Alastair leaves and Anandas tells Dean to take his ten minutes right then, to catch his breath. Dean does, and Mark goes with to comfort him. When his break is over, Dean goes back to work, thoughts whirling.

After that first day, Dean was a bit more wary of believing Anandas’ promises, but fell into the rhythm of being behind the bar easily enough. Most days, Mark hung out with him behind the bar. Most of the demon patrons seemed to give the wolf a wide berth, so when Mark was friendly toward Dean, they got the message, and left Dean alone.

But there were a few who didn’t seem to care about the wolf’s feelings - or Dean’s - who came to the bar seemingly just to bully Dean, in the hopes that he might end up displeasing Anandas, and be turned over to one of them for “punishment.” Abraxas hadn’t remained silent, and the rumors were flying that Dean could be had, if you were able to get him into trouble with Anandas.

The one saving grace seemed to be that none of them had realized the truth. It wasn’t that Dean had been in trouble with Anandas that had gotten Anandas to give Dean over to Abraxas. It was the fact that Anandas had made an error that would have made  _ him _ look bad to the higher-ups on Hell’s hierarchy, had it come to light, and by turning Dean over to Abraxas, Anandas had managed to get Abraxas to forget about reporting the mistake. So long as the trouble that the demons got Dean into only reflected on Dean, and not Anandas, Anandas wasn’t an unfair boss, and would just take it out of Dean’s tips, rather than letting the demons take it out of Dean’s hide.

For a couple of weeks, Dean slipped into the routine of working a 12-hour shift at the brothel’s bar, then being returned to Alastair for further torment - either by Alastair himself, or some other demon that Alastair chose - followed by some time in sensory deprivation, before Alastair returned to ship him back to the brothel. Dean never mentioned the incident with Abraxas to Alastair, at first because he figured that if Anandas had gone so far out of his way to avoid having Abraxas report it up the chain, he wouldn’t appreciate Dean reporting it, and afterward because the incident simply slipped Dean’s mind. What was one more torment, even one as vicious as what Abraxas had subjected him to? In the long term, it barely registered.

Until the night that Alastair came into the brothel’s lounge and sauntered up to the bar. “Hello, Dean. I’d like a bottle of Jager and a couple of cans of Red Bull. I’m in the mood to make up some Jager bombs.” 

Dean paled a bit, but since Anandas had, in fact, followed up and ordered more brands and types of liquor and mixers, he was able to pull out a bottle of Jager and two cans of Red Bull and place them on the bar in front of Alastair.

Anandas came out from the office to the bar just as Dean set the items on the bar. “On the house, Alastair.”

Alastair acknowledged Anandas’ words with a cordial nod of his head. “Anandas. Something you forgot to mention to me?”

Dean paled further, but another demon walked up to the far end of the bar and he had to go to serve them. He couldn’t hear the conversation at the other end between the demon who owned his soul and the demon who had charge of him for 12 hours a day. He took the tokens from the customer and put them in the register.

“Dean. C’mere.” Anandas beckoned, and Dean headed back to their end of the bar.

“Yes, Sirs?” Dean asked, warily.

Alastair smiled at him. “Dean, Dean, Dean. It seems you forgot to tell me something.”

Dean glanced at Anandas, but the owl’s face provided no clues. “Um. Did I, Sir? I-I’m sorry.”

Alastair tsked. “You see, Dean, I have a policy. When I loan out a soul that belongs to me, and that soul gets punished by the demon to whom I’ve leant it, I punish it as well, when it’s returned to me. But here, you were punished, a couple of weeks ago, it turns out, and no one told me anything about it until today.”

“I-I didn’t know that, Sir, that you had that policy, I mean.” Dean dropped his gaze to the floor.

“Hmm. That may well be. I don’t remember mentioning it to you. But see, Anandas here? He knew. He should have mentioned it to you. And he should have told me that he’d seen fit to punish you, and why. But he didn’t do either one of those things, did he, Dean?”

Dean whispered, “No, Sir.” He trembled.

“No. No, he didn’t. And you didn’t think to volunteer the information yourself. Dean. you really should start showing some initiative once in a while.” Alastair tsked again, and put a finger under Dean’s chin to raise it so he could look Dean in the eyes. “Now, I’m not angry with you, Dean. As we’ve established, you didn’t know there was a policy in place. And I suppose you might have thought that you should show Anandas here some loyalty, since he favored you with this cherry bartending job, instead of putting you to work as a whore in the back, as I had suggested.”

Dean shivered, but didn’t try to look away.

“Look, Alastair, I do appreciate the suggestion, but the fact is, the lounge needs a good bartender, and Dean here’s the best I’ve got,” Anandas stated.

“That may well be, Anandas. But you would do well to take suggestions to heart when they come from member of the Committee. You work for us, remember?” Alastair glanced over at Anandas for a brief second, then looked back at Dean, and smiled again. “So, Dean, since I’m not upset with you, I’m going to give you a choice. Which would you prefer? 

“Number one, you can continue to work here as a bartender, but you’ll move to twenty-hour shifts, and then go straight to sensory deprivation until it’s time for you to return here, for five days on, then two days with me for torture around the clock.

“Number two, you can choose to work here as a bartender, but you’ll move to a eight-hour shifts, then you’ll be a whore for eight hours, then be tortured by me or another demon of my choosing for eight hours, then come straight here without being healed to come to work again.

“Or, number three, you can choose to work here, but you’ll be a whore, for twenty-four hours on, then come to me for a torture assignment for the next twenty-four hours, then back here, in rotation, with no sensory deprivation at all. 

“Those are your choices, Dean. Choose one. But choose wisely.” Alastair gripped Dean’s chin a little tighter, and twisted slightly.

Dean considered, and made his choice. “Option number one, Sir - twenty hour shift as a bartender, then straight to sensory deprivation, for five days on, then two days with you for torture, Sir.”

“Lovely.” Alastair’s voice took on a grim tone. He twisted Dean’s chin a little more, then released it. “You’ve been here how long so far, today?”

“Two hours, so far, Sir.” Dean whispered.

“Then you have eighteen to go. Anandas, you can handle putting Dean in sensory deprivation when he’s done, and see that he gets to me at the end of the fifth day, can’t you?” Alastair suggested, but it was clear that the answer had better be yes.

Anandas nodded. “Of course, Alastair.”

“Excellent.” Alastair took the bottle of Jager and the cans of Red Bull from the bar and turned to leave. “I have a friend to celebrate with - his name’s Abraxas - and he just loves his Jager Bombs. Ta.” He walked out.

Dean gasped for breath.

“Dean, go take your ten right now. Go catch your breath. It’s fine. I’ll watch the bar,” Anandas told him.

Dean nodded weakly, and headed for the staff room. Once there, he sank down onto one of the couches along the wall, and set his head in his hands, elbows on his knees, fingers carding his own hair.

Mark pushed the staff room door open with his nose, and slipped in. He came over to Dean, and nudged Dean’s side gently, then put his front paws on the couch next to Dean, and nuzzled him softly. “Woof.”

“Hey, buddy.” Dean took a deep breath, and then scratched Mark’s ears. The wolf’s tongue lolled out of his mouth for a moment, but then he leaned in and licked Dean’s cheek. “Thanks, Mark.” Dean patted the couch and invited the wolf to come up next to him.

“Woof.” Instead, Mark got down, and curled up around Dean’s feet on the floor, obviously trying to give his friend some comfort. Dean leaned down and gave him a stroke, then leaned back against the back of the couch, and tried to breathe slowly, in and out.

After a few minutes, Mark got up, looked at Dean, and then the door. “Woof.” 

“Time to go, huh, bud?” Dean rose, and walked to the door with the wolf, letting him out first, then stepping out to head back to the bar.

“You all right now, Dean?” Anandas asked.

“Yeah. You?” Dean responded.

“I’m fine. I’m sorry about the sensory deprivation thing, man.”

“It’s fine. I chose it. Don’t worry about it. Look, let’s just… let’s just get back to work, okay? I just want to keep busy.”

“Sure. I’ll be in the office.” Anandas removed himself from behind the bar and slipped into the back.

Dean took a deep breath, and then turned to serve a customer. 

_ It’s fine. It’ll be fine. I can rest, sort of, in sensory deprivation. It’ll be fine. Why didn’t I tell him? It’s fine. He’s not mad. He said he wasn’t mad. It’s fine. _

“Yes, Sir, a White Russian, coming right up.” Dean turned to make the drink, thoughts whirling in his head.

***

**Notes for the Chapter:**

> Please comment! I really want to know what y'all think!


	11. Welcome to Stockholm, Dean

**Summary for the Chapter:**

> Dean finishes his shift; Anandas removes the collar and bracelets and puts Dean in sensory deprivation. Dean tries to relive his memories, but each time he thinks about John, it's "fuzzy" and almost painful, to the point that his mind skitters back from thinking about him. In the middle of a dream about the time he and Sam set off the 4th of July fireworks, Dean suddenly comes to, in "the bedroom," but Elena isn't there. He cannot see anyone, but he feels multiple hands and fingers on his skin, at first gentle and arousing, then painful and bruising. The touches turn from gentle fingers to slashing implement, like a crop or a switch, and he screams when particularly painful blows fall on his cock. The touches stop, and suddenly he's being untied...by Bela Talbot. Bela tells him that she can get them both out, but Dean doesn't trust her, and refuses to go.

Dean went through the motions for the rest of his shift, but his mind was elsewhere. 

_Alastair said he wasn’t mad. Was he lying? Is he angry? Does it matter? He tortures me when he’s in a **good** mood; how could it get **worse**? Maybe I don’t want to know…. _

Each time Anandas came out to the bar to relieve Dean for his breaks, the owl-demon had almost a sad expression on his face. Dean shook off any attempt on Anandas’ part to show concern. If Alastair was angry, it was Dean’s own fault. He should have known better, should have reported the incident with Abraxas, should have said something about it immediately, shouldn’t have let it fester. The fact that the situation was now putrid was something he’d just have to deal with, and Anandas couldn’t fix it, even were he so inclined. 

Besides, so far as Dean knew, he wasn’t so inclined. Anandas was out to protect himself. He wasn’t Dean’s friend, just his supervisor while he worked his shift. He’d promised to be a fair employer, but that only extended so far, and the rest was a lie.

_He’s a demon; demons lie._

His shift over, Dean was relieved by the next shift’s bartender, and went to the office to have Anandas remove the collar and wristbands.

“Look, Dean, I…”

“Forget it, man. I don’t want to talk about it, okay? It’s fine. It’s over, it’s done. I’ve just gotta get through, that’s all. You can’t help, that’s clear. So, just let it go.” Dean kept his eyes lowered respectfully, but squared his jaw.

Anandas sighed. “All right.” He snapped his fingers, and the collar and wristbands vanished. “I’ve gotta put you in….”

“Sensory deprivation. Yeah, I know. Just do it. See you tomorrow.”

And suddenly, Dean was floating in the dark, soundless existence that he’d come to almost love. He’d stopped panicking from the absence of sensation long ago, so long as the absence was total. When Alastair put him under only part way, and he could still feel pain, or still hear sounds, he couldn’t relax at all. When there was no sensory input at all, he couldn’t quite rest, exactly, but he could think and dream and remember, and that gave his brain some needed downtime.

Except that, lately, as he thought and dreamt and remembered, he found that some of his memories - almost all of them involving his dad, in some way - were a little...fuzzy, somehow. Most of his memories were sharp, clear; if he brought them forward, he could almost relive them. But a few, he simply could not bring into sharp relief, and the more he tried to do so, the _less_ detail he could actually remember. 

He found that more and more often, his brain went skittering around the unclear recollections, seemingly trying to actively avoid them, until he finally just gave up on thinking about John at all; he had better luck with his memories of Bobby or Pastor Jim, and the sharpest memories were those of just him and Sammy.

He was right in the middle of a dream about the time that he and Sammy set off fireworks in a field on the Fourth of July, when suddenly he was in “the bedroom,” naked, tied to the bed, spread-eagled. He looked around for Elena, but didn’t see her. In fact, he didn’t see anyone. But he felt a feathery touch run along his right leg, from just below his ankle to just above his knee. Dean shivered.

“Elena? Is that you?” he asked.

He could see no one, and he didn’t hear a voice. But in his mind there was the impression of a presence nearby. Then, he began to feel fingers and hands running over his skin gently, everywhere. The touches were soft and inviting, and made him tremble; suddenly, he began to struggle against his bounds. He wasn’t supposed to be here, he was supposed to be in sensory deprivation.

_Will I get in trouble for being somewhere I’m not supposed to be, even though I had nothing to do with being here? Seems likely, the way things have been going._

“Please, you have to put me back. I’m not supposed to be here. I’ll get in trouble. _Please!_ ” The touches only intensified, stroking him with care toward arousal - and then became painful, bruising. “Please, no. Please, please, put me back in sensory deprivation, where I’m supposed to be, please.” Dean sobbed, terrified of the potential for negative consequences, of Alastair’s potential anger.

The touches intensified yet again, blisters forming in trails following the sensations, then bursting suddenly to drip clear fluid. And then the tenor of the touches changed; rather than feeling like hands or fingers, now it was a crop or a switch, striking Dean’s flesh, but everywhere at once.

Dean screamed, tensing, back arched off the bed, as the invisible implement struck viciously along the length of his cock. And then, as if the scream had been a signal, it all stopped.

Dean sank back down into the bed, tears streaming down his face, his eyes closed.

The feathery soft, gentle touch, of just one finger, returned, as if in apology. Dean whimpered, a noise of pain and fear rather than desire.

“Shhh. Hush, now. Shhh. It’s all right.” Dean’s eyes flew open at the voice, and looked up, confused, at the face of Bela Talbot.

“Bela? What…?”

“Shhh. Relax. It’s all right now, Dean.” Bela untied his wrists, then moved to the end of the bed to untie his ankles.

“Are you all right to stand, Dean? Can you walk?” Bela got him up, and slung his arm over her shoulder and around her neck, sliding over to hold him upright.

“Bela, I’m...I’m supposed to be in sensory deprivation. I don’t know how I got here. If - when - Alastair finds out I’m not where I’m supposed to be, he’ll be furious, please, I have to get back….”

“Shhh, Dean, c’mon, come with me, I can get you _out_.” Bela said, insistently, pulling him along. Dean struggled against her, and finally pulled free.

“You can’t get me out! How are you even _here_? Why aren’t you in the Pit, being turned into a demon? You came down before me, you should be further along in the process, halfway to smoke by now!”

“Dean, I don’t have time to explain, but I promise, it’s really me, I’m really here, and I can really get us both out, but only if you come with me, right now, and stop fighting, because we’ll have to be quiet! Now, come on, or I’m leaving you behind.” Bela watched his face for a moment. 

_Bela_

Dean shook his head slowly, his eyes meeting hers. “No. I don’t believe you. Go. Get out, if you can. But I’m not running. I’d just slow you down, make it so neither of us got out. And if I got caught, I don’t even want to think about what Alastair’d do to me. So, go. Bye. Good luck.”

Bela sighed. “Fine. Have it your way, Dean. You always do. Y’know, we’re on the same side, here. But you could never bring yourself to trust me, or, God forbid, _help_ me. So fine. I’m not sure why I thought to help you, in the first place.”

She turned to leave, but Dean reached out and touched her arm. She turned back to look at him.

“Bela, I’m sorry that I failed you while you were alive. I don’t want to fail you again. Go. I hope you make it out.”

Bela leaned into Dean, and kissed his cheek.

Then she turned to go, and Dean was alone.

***

In his office, watching on the monitor, Alastair smiled.

***

**Notes for the Chapter:**

> Please comment!!!! Please! Is anyone reading this, despite the warnings? *sigh*


	12. Burning Exhaustion

**Summary for the Chapter:**

> Dean finds himself in a corridor with no notion of how to get back to where he's supposed to be. He decides to just rest and wait. Eventually Alastair comes for him and takes him back to the rack, but then decides he's in the mood for fire. So, Dean finds himself back in the pit, suspended from the hook and chains, being roasted. He breaks down and cries, and suddenly finds himself back in Alastair's rack room, only to be comforted by someone he knows well.

Dean watched Bela walk away until she turned down another corridor, out of sight. Then he heaved a sigh, and turned back, but the door they’d just come out of was no longer there; where it had been, there was just a wall. He started walking up the corridor in the same direction as Bela, for lack of anywhere else to go, trying doorknobs as he went; all were locked. He looked up and scanned the hallway. He wasn’t even sure of what he was looking for, until he saw it - the camera. He was being watched, probably by Alastair.

“Alastair, if you can hear me, I know I’m supposed to be in sensory deprivation now. I was there, and I didn’t leave it of my own volition. I don’t know how to get back, and I don’t know where I am, or how to get to you, either. This corridor isn’t somewhere that I remember having been before, and I don’t know where to go from here.” He spoke clearly, thinking that even if there was no sound, perhaps Alastair could read lips, or would at least be intrigued enough to want to know what he’d said.

Dean leaned back against the wall, and sank down until he was crouching near the floor. He was exhausted. There was no point in running. He had no idea where he was, nor how to get out, or even to anywhere he’d recognize, from here. He might as well stay here, and rest, until someone eventually missed him and came to get him. He’d probably be punished, but he was too tired to care. He closed his eyes and leaned his head back against the wall.

***

“Hello, Dean.” Dean looked up at Alastair’s voice. Alastair was standing above him in the hallway, hand extended. “Let me help you up.”

Dean took the demon’s hand, and Alastair hauled him to his feet. “Have a good rest, Dean?” The demon’s voice was unexpectedly mild.

Dean kept his eyes on the floor. “I know I’m not where I was supposed to be. I apologize.”

“No worries, Dean, I know it wasn’t your doing. But let’s get you back to where you’re supposed to be, hmm?” Alastair snapped his fingers, and they were back in his own private torture room, Dean strapped to his rack.

Dean looked up, startled. “I thought I was supposed to serve….”

“In the brothel for five days, yes. But you had. So, when Anandas put you in sensory deprivation after your shift last night, you were always coming back to me for my two days of fun with you. Which is why you’re not in trouble. I sent the succubi to you last night. And you were very good about begging to be put back where you thought you were supposed to be, Dean. Good boy.

“Now, then. I think this morning, I’m in the mood for _fire_.”

***

Dean found himself back in the vast empty space in which he’d begun his stay in Hell, meat hook in his shoulder, chains attached to manacles on his wrists and ankles holding him spread-eagled in mid-air - but now there were two distinctly different characteristics of this area. For one thing, Dean wasn’t alone, this time. There were thousands of… souls? entities? … similarly hung up on display, some close enough that if he wasn’t stretched out so tautly by the chains, he might have been able to touch them. For another, that original space hadn’t had these flames that he now felt licking at his skin.

As before, Dean was clothed - t-shirt and jeans, socks, and boots - and after so much time naked or in the shorts he wore at the bar, being fully dressed felt bizarre. Then the jeans caught fire, and Dean had a pretty good idea of why they were there - to hold the fire against his skin for longer and in a way that was more damaging than the flames in midair would have been on their own.

First time around, being here hadn’t been that bad. Now, it was excruciating, and Dean wasn’t sure if having others around made it worse, or better. He could hear the others’ screams, and he didn’t want to add to the cacophony, but the burning denim holding the flame on the skin of his legs, which was already starting to bubble, was already making him whimper. He scented roasting meat, knew it to be his own flesh, and knew the screams were on their way. 

The metal hook in his shoulder started to glow, and he felt the heat of it passing through him, and now it felt like his muscle was melting from the inside, and he couldn’t hold back any longer; the scream won, and he let it go. It erupted from his throat, full-bodied and deep, and the soul to his right, which looked to be a middle-aged man with a comb-over, looked over at Dean, and nodded.

“That’s it. Let it out. It doesn’t help, but every now and then, it’s just necessary,” he said. 

Dean nodded back. “How...long…?”

“Have I been here? Dunno, lost track a long time ago. People come and go. Sometimes they’re there for thirty, forty years; other times, they’re there, then gone again in a blink.”

“Will we get in trouble for talking like this?” Dean asked.

“Nah. I mean really, what’re they gonna do, right? We’re already dead and on fire. It’s like having your former boss call you at home after he’s already fired you in order to chew you out for something else he thinks you did wrong.” The man laughed. “What’re they gonna do? Fire me again?”

Just then, the flames rose higher and engulfed him.

“Really? Seriously? Oh, sure, very funny!” the man exclaimed. “I say ‘fire me again’, and so you turn up the flame? Hah!”

“You don’t even seem bothered by it,” Dean noted.

“Eh, the fortieth time your skin bubbles up off of you in the flames, it gets a little old. I almost wish they’d decide I was ready for some new torment, but, then again, I’m sorta gettin’ comfortable right here. I think I’m gonna take a little nap.” The man closed his eyes, and let his head loll to one side, and, amazingly, did actually seem to be sleeping, despite the fact that his suit was on fire, which could not have been at all comfortable.

Dean whimpered. He didn’t  _ want  _ to become so comfortable with being on fire that he’d be able to sleep through it. He tried to focus on his memories, to have something besides the pain that he could focus on, but, again, they seemed to whirl and fracture, becoming slippier the more he tried to get a solid grasp on them. He tried again to make Sam his focus, the clear memories of his brother the one thing he could hang on to reliably.

Thinking of Sam, though, made him realize, yet again, that he still didn’t know if Sam was dead or alive. He couldn’t imagine that Lilith would have left Sam whole after Dean had died, but no one here seemed to know for sure where Sam was. Thinking of the possibility of Sam being here, somewhere, on a hook, in chains, on fire, brought the tears that Dean had, until then, been able to suppress, and he began to blubber helplessly.

***

Suddenly, Dean was back on Alastair’s rack, whole, unburnt, and naked once again, each leg bound separately and apart, arms bound straight out to the sides. He sighed softly, and kept his eyes lowered, looking at the floor.

Someone stepped into view, between Dean’s legs. A hand came up and gently gripped Dean’s chin, lifting his face so he had no choice but to look up at them.

“Hello, Dean.”

Dean looked up, startled, into the face of ….

“ _ Dad _ ?”

“Hey, kiddo. I’ve only got a moment, and though you can see and feel me, I’m not really here; I’m up in Heaven. But yeah, it’s me. I just came to tell you, there are entities up here, working to find a way to get you out. Keep resisting, don’t take Alastair’s deal, and if an angel comes for you, you go with them without a fight. You hear me, boy? Proud of you.”

_ John  _

John started to fade from view.

“Dad - quick, please, just tell me - is Sammy alive?” Dean got out.

John’s mouth moved, but made no sound. Just as his visage slipped out of sight, though, Dean thought he might've caught the edge of John’s nod.

***

**Notes for the Chapter:**

> Was it really John? Or a vision planted by Alastair? Hmm. 
> 
> Please comment!!!


	13. Exhaustion Sets In

Alastair moved Dean with such frequency from one stress situation to another, one location in Hell to another, one torturer to another, that Dean started to lose track of where he was and what was being done to him at any given point in time. 

… Alastair was cutting ...

… the invisible succubi were stimulating him sexually to the point of pain ...

… sensory deprivation ...

… on the hook, being roasted in the flames ...

… a smoke demon was bending him over and raping him anally …

...and back to being on Alastair’s rack, but alone in the room, tears and snot dripping down his face, chest heaving from the sobs he could no longer choke back.

Dean tried to take a deep breath, tried to get his panic under control. He was alone, and while on the rack, nothing was being done to him. He was whole and unhurt again. 

But while Dean knew that, rationally, he was dead and none of what he was experiencing was  _ real  _ \- it was all just illusions, mind games being played on him - he found that he was having a very hard time finding any kind of calmness within his soul at the moment. His mind, his soul, was all there was left of him, and the games were working too well. The tortures were too many, too varied, coming at him too fast, for him to find any way to take himself mentally out of them and calm himself down, such that, again, even being given a chance to rest, as it were, was freaking him out. 

He drew a shuddering breath, and tried to hold it for a count of four, then to let it out slowly. In for four, hold for four, out for four. In for four, hold for four, out for four. Finally, he felt like his lungs were relaxing and he was getting some air.

And just as he started to feel better, Alastair came in from the next room. “Hello, Dean.”

Just like that, Dean’s heart started to race, but he tried to continue the breathing pattern, keeping his eyes lowered respectfully, not responding verbally, as he knew Alastair preferred unless a direct question had been asked.

Alastair stepped over to him, hooked Dean’s chin on one finger, and raised Dean’s head until their eyes met. Alastair smiled. “There you are.”

Alastair released Dean’s chin and snapped his fingers. Dean’s bounds released, and he fell forward to the floor, scrambling to get into his proper position, one Alastair had altered just a bit from the initial position on Abraxas’ recommendation: Dean’s ankles crossed, knees spread as wide as possible, back straight, head down, hands resting with palms turned up on his mid-thigh, where they shielded nothing, eyes fixed on a point on the floor about a foot in front of his knees, right in front of Alastair’s feet.

Alastair reached forward and ruffled Dean’s hair gently. “Such a good slut. Your training really is going very well.”

Dean winced internally, but was careful not to let his facial expression change outwardly.

“So, Dean. Are you ready to take me up on my offer yet?”

“Scr...ew…. You….” came the soft reply.

“Ah. Not quite so belligerent about it now, at least. But still a no, I see. Well, that just means I still have work to do. That’s fine. I didn’t expect it would be easy to convince you to join us, Dean.” Alastair smiled benevolently. “I suspect you might be feeling a tad lonely, so I decided to bring you a friend. You can watch me torture them, and that will, I believe, torture  _ you _ . In a way, you really have Meg to thank for this; she suggested it.”

Dean’s mind whirled. _What did Meg suggest?_ _Oh...shit...no!_

Dean felt a presence to his left, and tried to subtly glance in that direction.

“No need to hide it, Dean. Go ahead, look and see who’s here,” Alastair told him.

Dean turned his head slowly, wanting to see, yet dreading it as well. And, as he had suspected, Sam was kneeling next to him, looking like he’d been through the wringer; bruised, bloodied, whip marks criss-crossing his skin. Clearly, whoever had been torturing Sam had not been healing him, as Alastair had been doing for Dean.

Dean tried to keep it in, but a gasp escaped him, first at the almost-not-a-suprise of seeing Sam in Hell, but secondly due to Sam’s poor condition. Dean tried to reach out a hand to comfort Sam, and found himself suddenly bound tightly again to Alastair’s rack.

“Tsk tsk tsk. I said you could look, I didn’t say you could touch.” Alastair’s whiney sing-song voice said.

Dean whimpered. He closed his eyes, not able to bear looking at Sam in the shape he was in. He knew that Meg had been correct when she’d said that the best way to torture Dean was to bring Sam in and torture Sam in front of Dean, with Dean having no way to stop it or make it any better. Obviously, Alastair had come to the same conclusion.

“Sam,” Alastair said, almost gently. “Stand up for me.”

Sam rose slowly and gracefully to his full height, but kept his head bowed respectfully, his hands behind his back as if they were bound there, though they were not.

“Step up to the table, hold the sides of it with your hands so they’re spread wide apart, and bend forward. Spread your legs, and bend your knees a bit, as well; that’s it, that’s lovely.” Alastair moved up behind Sam and corrected his position gently as necessary to get him to where Alastair wanted him. Sam gripped the edges of the table, his knuckles white, as he waited to see what would happen, but gave no other indication of his feelings. Alastair knelt behind Sam and tied his ankles to the table legs to keep them spread, then rose again. He turned to Sam’s left side, so that Dean had an unobstructed view of his brother’s backside; he looked at Dean, and grinned; then he manifested a riding crop and began to whip Sam’s ass and the back of his legs. Sam didn’t move, didn’t make any noise, didn’t appear to object in any way, but his breathing grew labored as the whipping continued.

Dean’s face was still wet, his eyes already red, from his earlier tears, as Alastair had neither given him an opportunity to wipe his face, nor done so for him. Seeing his brother being abused, and apparently being so used to such treatment that it had such little impact on him, caused fresh tears to fall. Dean himself had not yet reached the level of pain tolerance that would allow him to take a severe whipping like that without screaming, much less without making any noise at all….

And that’s when Dean realized: it wasn’t really Sam, not  _ his  _ Sam, not his real brother, but an illusion. Perhaps a demon with a facade, perhaps just a simulacrum created in some other way, but that was not his Sammy. Sam had never been good at handling pain - he could dish it out, but a splinter would have him blubbering - and there was no way he’d be able to take a beating like that and do nothing more than breathe a little harder than normal.

_ Alastair is a demon; demons lie.  _

But then Dean realized further that he needed to make Alastair  _ believe  _ that he thought the illusion was real. He had to act as if it  _ were _ really his brother there being beaten in front of him. As it was, Dean wasn’t being tortured - except psychologically, which, since it wasn’t really Sam, he could handle fine - and he needed to keep it that way for a few more hours, just until it was time for his next shift at the brothel’s bar. He needed the rest from the pain that he was currently getting to continue until then, or he might not be able to make it through a 20-hour shift on his feet with only 10-minute breaks every 4 hours. So…

Dean whimpered, and continued to let the tears fall, and tried to sound pathetic without overdoing it. “Please, don’t… stop hurting him, please.”

As Dean had hoped, Alastair simply laughed quietly, continuing to rain blows down upon the fake Sam’s body.

***

Weeks passed. For five days straight, Dean worked his 20-hour shifts at the brothel’s bar, then got his 4 hours of “rest” in sensory deprivation. At least with Anandas putting him in SD at the end of each shift, the sensory deprivation was complete - there were no lingering aches or sounds or other distractions that could pull his focus away from trying to keep his memories of his brother as sharp as possible.

Dean found that he could no longer think of John at all; it was actually painful, like a sharp stabbing in the center of his brain, to try to focus on specific memories of his father. Oh, he could pull up John’s image and recall what he looked like well enough; but if he tried to remember a specific instance of something that happened between the two of them, he couldn’t do it without wincing and giving up. Eventually, he simply stopped trying, his mind skittering away from the attempt.

He could remember certain events that involved both John and Sam; the night of the fight about Sam leaving for college, that was perfectly clear. Finding John in Chicago right after the daeva attack, when he’d hugged both of them, that, too, was like crystal. But Dean had to focus on remembering the events  _ as they pertained to him and Sam _ or that odd sense of danger, pain imminent, would return.

He had the odd feeling, too, that his memories of his father, in general - of John’s attitudes, beliefs, and the way he’d treated Dean and Sam - were somehow changing. But because he couldn’t pull the memories forward clearly without pain, he couldn’t figure out what the changes were, and, over time, the sense that they were changing faded, seemed unimportant, and he gave up chasing after it.

The two days in between were unrelenting agony, as Alastair and the other demons put Dean through 48 hours of unending torture, his only rest coming from the occasional times when Alastair would introduce a third party to be tortured before Dean - usually Sam, but sometimes Bela Talbot, or Layla Rourke (Dean wasn't even certain that Layla had died, though she had certainly been ill enough during the short time he'd known her to have died by then; but why would someone with a faith as strong as Layla's end up in Hell? - or even, once, Mary Winchester (and who knows where her spirit had ended up after it had been expurgated from their old family home when he and Sammy had returned to Lawrence due to one of Sam's visions?). Dean could not know if these entities were the real person they were made out to be, or not; he believed - hoped - they were not, but he pretended otherwise, and Alastair, so far, seemed not to see through his pretense.

***

**Notes for the Chapter:**

> Hello! No art this time, sorry. 
> 
> However, might I interest you in a new story? I just today posted the first chapter of Two Nuns Talking, which is not part of this series at all and has no connection, other than having the SPN characters in it. Find it here: https://archiveofourown.org/works/28667871/chapters/70277250 - please let me know what you think!
> 
> And please comment HERE and let me know if you are reading this (I won't say enjoying it, because torturing Dean isn't fun, as we all well know, which is why no one EVER does it, right??). ;)


	14. Inventory. Mmhmm. Right.

**Summary for the Chapter:**

> Alastair sends Dean back to the brothel too exhausted to work. Anandas takes one look at him, and makes him take a nap. Abraxas shows up partway through Dean's shift and demands to know where Dean is. Anandas lies and says Dean's in the back, taking inventory. Abraxas says he's been speaking with Alastair and knows Dean's choice, and it wasn't anything to do with inventory, he's supposed to be working the bar. Anandas gives in and goes to get Dean from the storeroom - except Dean's in his office, so he has to make a show of going in the storeroom and then secretly teleport. They get rid of Abraxas, but Dean realizes that Alastair will likely eventually find out, in some way, from some source, that Dean was sleeping on the job, and that they lied to Abraxas, and if Dean doesn't tell Alastair himself, first, his punishment will be worse than he can probably handle.

Alastair released Dean from the rack; Dean scrambled to get into position properly, but suddenly realized Mark was in front of him, gently pawing his leg and licking his face. Dean looked up and found himself kneeling in Anandas’ office. The ‘weekend’ was over. He breathed a sigh of relief, and reached a hand up to give Mark’s ear a gentle scratch. The door opened, and Anandas stepped in.

“Mornin’, Dean,” he started, then looked - really looked - at Dean. “Oh, that is _it_. I’m going to have to have a word with Alastair, he can’t give you back to me for a 20 hour shift looking like you’d fall over if a strong enough breeze hit.”

Dean panicked. “No, d-don’t! I can w-work! I c-can do it! Really, Sir, I…”

“Stop. Dean, stop, I’m not angry with you. It’s okay.” Anandas reached down and gently helped Dean to his feet, led him over to the couch, sat him down, and got him a soft blanket. “When was the last time you really slept?”

Dean just shook his head. He couldn’t remember.

“Take a nap, Dean. That’s an order. You look like hammered crap. Lay down right there on my couch, and sleep. Mark will stay with you, and I’ll go tend the bar.” Anandas sighed, and stepped out of the office. 

Mark curled up on the floor below the couch, just within Dean’s reach. Dean shrugged, laid down, and pulled the blanket up over himself. He stretched one arm down to pet the wolf gently, and left his hand resting on Mark’s back as he closed his eyes, and fell straight into a dreamless sleep.

***

Anandas came back to check on Dean at his first scheduled break time, four hours later. Mark raised his head and growled softly. 

“Hey, buddy,” Anandas said, quietly. “I’m not gonna wake him. I’m just lookin’ in, seeing how he is. You’re taking good care of him, I trust.”

Mark settled back down. Anandas reached down and touched Dean’s forehead lightly; he concentrated,using his limited healing power to fix a few things and give Dean more energy. Then he went back out to the bar, leaving Dean to continue his nap. 

As Anandas stepped back behind the bar and started to wipe down the counter, Abraxas walked into the lounge. 

“Well, well, well. Andy. Surprised to see you behind the bar. Where’s Dean?” Abraxas asked, mildly, yet malevolently.

_Abraxas_

“In the back, doing inventory. As you’ve pointed out, Abraxas, ordering isn’t my forte. Dean’s good at keeping track of things.”

“Is he? Well. That’s lovely. Except Alastair and I have been talking about Dean a good bit lately, and he told me of Dean’s choice of how to serve. And the deal was that Dean was supposed to be out front behind the bar. Not in back, doing inventory.”

Anandas tossed the rag he’d been using to wipe down the counter aside with a sigh. “Fine. You’re the one who complained that we didn’t have your drink in stock. But you’re right. Dean’s choice was to serve up front. I’ll get him. Be right back.”

Anandas turned, got a can of Red Bull and a bottle of Jager, and set them in front of Abraxas. “On the house. Any friend of Alastair’s, etc., etc.” Then he turned and walked down the hall toward the store room, which was on the same side of the bar as the staff room - away from his office, where Dean was sleeping. He entered the storeroom, then teleported himself to his office, hoping that Abraxas wasn’t aware he could do that. 

“Sorry, Mark, but it’s an emergency, Dean has to get up now, Abraxas is out front,” he told the wolf. Mark whined softly, but moved away from the sofa to let him approach and wake Dean. He put a hand on Dean’s shoulder, and shook him gently. “Dean? Dean. You’ve gotta wake up now. C’mon, Dean, time to rise and shine, let’s go, gotta get up now.” He shook Dean again, and Dean slowly started to react.

“Whatshappenin’?” Dean asked, blearily.

“Abraxas is out front, wondering why you’re not. I told him you were in the back, doing inventory, because you’d proved that you were better at it than I. He demanded that you be produced. So, I ducked back to the storeroom, then teleported here. Now, I’ve gotta teleport both of us to the storeroom, and get you out front looking _awake_. So.” Anandas materialized a cup of black coffee. “Drink this.”

Dean took the coffee, and downed it. The mention of Abraxas was enough to shock him the rest of the way awake, but the caffeine would help him to remain so.

“Okay. I’m up. Let’s go.”

“Hold up.” Anandas stopped Dean from rising, and leaned in to put the brothel’s collar around Dean’s neck. “Hands?”

Dean held up his hands, and Anandas slipped the wristbands on each of his wrists. Then Anandas snapped his fingers, and Dean was wearing a pair of worn, thin jeans that hugged his legs. 

“No shorts?” Dean asked.

“Not to do inventory. Besides, you look just as hot in jeans as you do in the shorts.” Anandas clicked his beak in a manner highly suggestive of a grin, and Dean grinned back. “Okay. Hold tight, let me get us to the storeroom.” Dean clutched Anandas’ hand, and blinked, and they were in the back of the storeroom, with Dean sitting on a box, Anandas leaning over him slightly.

“Nice landing.”

“Thanks. All right, we’re moving too slowly, here. Let’s get you out front.”

“Right.” 

Anandas led Dean out of the storeroom and back down the hall to the bar. “All right, Dean, I guess I’m finishing the inventory, but thanks for getting so much of it done. You did a great job; I’ll take it from here. Remember, you’ve got a break coming in a half-hour.”

Dean nodded. “Yes, Sir.”

Dean grabbed the rag, and started to wipe down the counter.

Abraxas snorted. “Inventory, huh?”

Dean shrugged. “It’s work, it needed doing. Dean can count.”

“Heh. Funny. Why’d it take Anandas so long to get you out here?”

“I was in the middle of a shelf, didn’t want to leave it, asked him to let me just finish that up quick. Sorry if it wasn’t quick enough, Sir.”

Dean kept his eyes respectfully lowered, but watched Abraxas in the reflection from the highly-polished bar. He could tell Abraxas wasn’t satisfied, but didn’t have enough to prove anything was really wrong. Dean breathed a quiet sigh of relief as the demon finished his drink, set down the empty bottle and can, and hauled himself up off of his bar stool. 

“I’ve got my eye on you, Dean,” he warned.

Dean nodded respectfully. “Yes, Sir. Thank you, Sir.”

Abraxas grunted, but again, couldn’t find fault with Dean’s demeanor or manners. He wandered out of the lounge, and Dean sagged against the bar for a moment. Then he felt a wet nose poking against his hand, as Mark came up behind him. Dean turned, and went down on his knee to give Mark a quick hug and a solid head scratch.

“Thanks, buddy,” Dean whispered to the wolf. Mark gave a quiet whine, and licked Dean’s hand, then went to lay down in his typical spot behind the bar.

Dean took a moment to breathe, and to look around. The lounge was quiet, only a few patrons sitting at tables, chatting quietly and sipping on drinks, making them last. _Likely on their last tokens,_ Dean thought. That meant that, for the moment, he had nothing to do, really. Oh, he could pretend to keep wiping down the bar, but it was already spotless. He could rest a little, even though he wasn’t sleeping. That six hours’ rest had worked wonders, but Alastair would be pissed if he found out about it. And to be sure that no one else told Alastair first, Dean would have to, as Alastair put it, “show some initiative,” or he’d likely be punished when Alastair inevitably _did_ find out about it.

Dean didn’t want to rat Anandas out and get him in trouble; for the most part, he liked the owl demon. But he knew if push came to shove, Anandas would throw _him_ under the bus - he'd already done it. Regretted it, but he'd done it. And he'd likely do it again. Which meant just one thing. Dean had to tell Alastair that he'd had a nap at Anandas' order.

***

**Notes for the Chapter:**

> Was the nap really worth it? *sigh*
> 
> Art!
> 
> Please comment! I really would like to know what people think of the story, and if anyone's even reading it, despite the warnings! ;)


	15. Forgiveness, a Return to a Previous Schedule, and Sex Work

**Summary for the Chapter:**

> Dean gets back to Alastair, and tells him about the nap and the lie to Abraxas. Alastair rescinds Dean's punishment detail, and puts him back on a rotation of 8 hours at the brothel, 8 hours of sensory deprivation, 8 hours of torture. Anandas dislikes losing Dean's 20-hour shifts at the bar, and punishes Dean with a shift of sex work. The demon that buys Dean's time doesn't want Dean's pain or humiliation, but his shame at having enjoyed what it did with the demon, and wrings pleasure from Dean until he's a sobbing helpless mess.

Dean didn’t get a chance to tell Alastair anything until much later. His five-day 20 hour shift then 4 hours in sensory deprivation didn’t let him get away from the brothel at any point, and Alastair didn’t come in. But on the sixth day, he went straight from behind the bar, to Anandas’ office to have the collar and wristbands removed, to Alastair’s rack, with Alastair already scalpel in hand.

“I..I need to tell you something, Sir,” Dean got out as Alastair took the first slice, out of the back of his neck this time.

“Oh? What’s that, Dean?” Alastair didn’t even look up, just continued to slice, as per his usual.

“The first morning that I was at the brothel this past week, I came straight from you to Anandas’ office, and he said I looked like h-h-hammered crap, and he ordered me to take a nap on the couch in his office, w-w-wouldn’t let me go out to the bar to work, even though I said I could do the w-w-work. Abraxas came in, asked Anandas why  _ he _ was tending bar instead of me, and Anandas told him that I was doing inventory in the storeroom. Abraxas demanded that I be produced, so Anandas went to the storeroom, teleported to his office, w-w-woke me, teleported both of us to the storeroom, and brought me out front quickly enough that although Abraxas was suspicious, he couldn’t prove anything. So, I took a nap when I was supposed to be working, and I participated in the lie to Abraxas. I...I’m sorry, Sir.” Dean hung his head, staring at a spot on the floor in front of him.

“Okay. Thanks for telling me, Dean.” Alastair’s voice was his normal, nasally, slightly high-pitched tone; it didn’t sound like he was upset at all. Dean dared to glance up, and saw that Alastair was smiling softly at him.

“Dean, I can see that you’re confused. Let me explain something to you. I already knew that you had taken a nap, I already knew that Anandas had lied to Abraxas, I already knew that you had participated in the lie. Did you think I wouldn’t have security cameras installed in the brothel’s lounge, the storeroom, and the owl’s office? Really, Dean?” Alastair laughed. “I just was waiting to see if you’d tell me, or not. And you did. So, good job, you’re not in trouble, and while you’ll be tortured, of course, it won’t be any worse than usual. I’m not upset with you. Anandas, on the other hand…” he trailed off.

“Please, Sir, Anandas was only acting out of concern for the brothel. He said he couldn’t put a bartender up front who looked as bad as I did that morning, because no one would believe I had authority to cut them off if I looked like that. The patrons have to know that I  _ am _ in charge of the liquor, that they can’t just jump the bar and take what they want, but if I had been out front looking as exhausted as I did that day, they might have taken advantage, or tried to, at least. He wasn’t acting out of concern for me, though that might have been a secondary concern. It was for the bar, and its inventory.”

“Hmm.” Alastair considered that. “So, you’re saying that Anandas ordered you to take a nap and went out front instead of you in order to protect my investment, in both the bar and, secondarily, in you, then?”

“Yes, Sir,” Dean nodded.

“If that was his motive, Dean, why lie to Abraxas? Why not just tell him that you were asleep in his office for the good of the bar?”

“Well, Sir… Abraxas already ran to you once with a tale of Anandas’ shortcomings, even after Anandas gave me to him to shut him up. I suppose Anandas didn’t feel that he could trust Abraxas not to tell you and put things in the worst possible light.” Dean mentally crossed his fingers.

“Wait. What?” Alastair looked genuinely confused. “When did Anandas give you to Abraxas to shut him up?”

“The first time that Abraxas came in, Sir. He wanted to make Jager bombs, but we didn’t have Jager or Red Bull available; Anandas hadn’t thought to order any. I told him that I had the ingredients for a bomb.com and could make him one of those instead, but he wasn’t having it, insisted on talking to Anandas. So, I went to the office and told Anandas there was a patron who wanted to talk to him about what drinks were available, explained the situation, and then went back out front while they talked. Then Anandas came out, and took off the wristband that lets patrons know that I’m not to come out from behind the bar without Anandas’ permission, and gave me to Abraxas. Abraxas dragged me back to one of the rooms used for sex work that was then available, and….”

“Yes, I get the picture. Did he just use you sexually, or was there anything else?” Alastair asked.

“He also whipped me, Sir. Anandas healed me before sending me back to you.”

“Why didn’t you tell me that Abraxas had used you, and that Anandas had to heal you afterward, Dean?”

“I thought you knew, Sir.”

“Dean, Dean, Dean. New rule. From now on, if anything at all out of the ordinary happens at the brothel during your shift, you’re to tell me first thing, the very next time you see me. Understood? In full, from your point of view. You see, Dean, I have certain sources of information, and most of them are very useful. But some of those sources shade things a little, some quite a lot. It helps me to get as many viewpoints as possible about every situation. Even watching the security cameras, I can miss things; I certainly missed you being taken from the bar area by Abraxas. 

“I believe I owe you an apology, Dean. I thought you were hiding things from me, and you  _ were _ , but I think now that it was mostly just from confusion on your part about what I did and didn’t know, and what I did and didn’t  _ want  _ to know. So, I’ll tell you what.. We’ll just forget all about that entire episode with Abraxas and the Jager bombs, and I’ll rescind your punishment and you can return to your initial eight-hour shift at the bar, then eight hours in sensory deprivation, then eight hours with me and my team. What do you say, Dean?”

“Um… all right. Thank you… Sir.”

“And while we’re at it, Dean, I haven’t asked you since your punishment began; are you ready to accept the deal yet? We could end all this nasty pain for you today, you could take up your role as my apprentice, and get started with that. No going back to the bar at all, then. What d’ya say, Dean-o?” Alastair smiled, but it was a nasty smile, and Dean didn’t trust it. 

It gave him the confidence he needed to say, once again, “Screw you and your deal. No.”

“Very well.” Alastair sighed, but the smile got bigger. “I guess then that I’ll just take my disappointment out on you while you’re here, then.”

***

Dean was just starting his shift at the bar, looking over the stock they had out, and wondering if he should go back in the storeroom to pull up some more whiskey, since they seemed a little low, when Anandas came out of his office to the bar, looking harried and distracted.

“Dean. I”m shorthanded today. Give me your wrists, please.”

Dean held out his hands warily. Anandas removed both wristbands, which he’d only just put on Dean about ten minutes prior.

“What’s going on?” Dean asked.

“I told you, I’m shorthanded. I’ll work the bar, you’re being reassigned. Head down this hall to Room 267, go in, lay down, someone will be with you shortly.”

“You’re putting me in for sex work? But….”

“I told you, you could have been doing it from the beginning. It’s just for one day, maybe not even the whole shift. Now, you have your instructions; get going.” Anandas stepped behind the bar and ignored Dean’s sputtering. Then he snapped his fingers, and Dean was naked. “Almost forgot.” 

Dean took a quick look around the almost-empty lounge; no one had seen, yet. He took a deep breath, and headed down the hall to Room 267, as instructed; if he stayed in the lounge, someone  _ would _ see, and going forward as the bartender in charge would be difficult, as he was sure Anandas had intended him to realize.

He found Room 267, and ducked inside. It was empty, which was some comfort, at least, for the moment. He laid down on the bed, as instructed, and tried to calm his breathing. He started to relax as the room remained empty but for himself, and yawned. Figuring it’d be a shame to waste the bed, he closed his eyes. He drifted off to sleep immediately, still exhausted from Alastair’s constant use.

He wasn’t sure how much time had passed when he woke, the room now dark. He wasn’t sure what had awakened him; a noise, a touch? He heard a soft laugh, and strained to see who else was in the room with him.

He still had not located the source of the laughter when suddenly his hands were snagged and dragged up over his head and secured to the head of the bed, not so tightly as to be painful, but securely.

“Hello? Who’s there? Please, don’t hurt me.” Dean was frankly terrified. He still could not see anyone, but now he felt a hand on his right ankle, as it, too, was secured to a corner of the bed.

Dean kicked out with his left foot, and tried to pull away as the invisible hand found that ankle, as well. He failed, and it, too, was secured to another corner. The invisible hand trailed up Dean’s leg, and hovered near his hip. Then he felt it sliding around to the base of his cock, circling it gently, just one finger tracing the length. Dean whimpered, and strained against the bonds.

“Shhhh,” he heard. “So pretty. Lay still, now, let me touch.”

“P-please,” Dean stuttered. “I don’t want….”

“What  _ you  _ want doesn’t matter, little one. You belong to me right now. What  _ I _ want matters.  _ My  _ pleasure.  _ My  _ desires. That’s all that matters, here. I won’t harm you. You won’t need to be healed when I’m finished with you. You needn’t worry about that. I’m not after causing you pain.”

“What, then?” Dean wondered.

“I’m after another emotion. I’m going to make you feel good, and you won’t be able to deny that you like what I do to you. And then, you’ll remember that I’m a demon, and you’re a whore, and you’ll feel ashamed. It’s your  _ shame  _ that I want. It feeds me. And you’ll give it to me, make no mistake, slut.”

The invisible hand continued to gently stroke Dean’s shaft, and Dean could feel himself getting hard against his will. It  _ did  _ feel good. There hadn’t been much in the way of gentleness for Dean in Hell, beyond the one time with Elena the succubus actually making him feel good, instead of too much, and he shuddered now, feeling the soft stroking fingers that he could not see sliding along his length, up, down, around, the blood filling his cock involuntarily.

Dean whimpered, and a tear slid down his cheek.

“Ah, good. Such a delicious appetizer. I think this will be a delightful meal.” The invisible demon’s voice was low, rough with satisfaction and need. It made Dean shiver helplessly.

The demon slid a cockring down over Dean’s now hard shaft. Dean realized it wasn’t going to allow him to cum, at least not anytime soon.

“If you have an orgasm, it will be my decision, slut. I will decide, because you belong to me, here, now. I’ve paid for this time with you, and I can do just as I like. I own you, for the moment. For this time, you have no choices. You do as you’re told, you obey, and you feel what I want you to feel, when I choose to allow you to feel it.”

Dean squirmed, trying to escape from the inexorably gentle touch, which somehow felt wonderful, but awful at the same time. It made not a hint of a difference; he couldn’t move enough to get away, and the demon simply laughed at his effort.

“Relax, pet. It won’t hurt you physically at all.”

Dean shook his head. “Please, please stop, please.”

“That’s enough of that, slut.” Dean suddenly found himself gagged, a thick ball gag in his mouth and secured around his head before he’d even realized he’d opened up for it. He coughed behind it at the taste of the rubber on his tongue.

“You don’t get to decide, pet.  _ I do _ . So there’ll be no more begging for me to stop. I intend to use you quite thoroughly. You’ll be wrung out when I’m through. But at every stage of it, you’ll feel good, so good, that you won’t be able to resist giving in to my desire, and at the end, I’ll remove that gag, and you’ll beg me to allow you to cum for me. You won’t want to beg, but you will. And when I finally allow it, you’ll know that I owned you, owned your orgasm, that it belonged to me, that you belong to me, in this time, here and now, and you’ll feel that, intensely. And that hot, thick shame will be like mother’s milk, to me.”

Dean shook his head again, tears falling, his face blushing hotly, red out to the tips of his ears, as his body betrayed him, aroused at the words and touch of the demon. The demon just laughed softly again, and stroked Dean’s thigh.

“I’m going to ride this lovely hard cock now, slut. I’m going to ride you gently, make it so good, so hot, you’d beg for it, if you could. And I’ll know just what you’re feeling, the hot slick pool of desire mixed with horror, the reluctance to admit that you want to be taken, used, that you want to be helpless and unable to resist. But in the end, you’ll have to admit it. I’ll make you say it. I’ll make you tell me that you belong to me, that you want what I do to you, that you love the way it feels. And you will say it, Dean. Willingly. You won’t have a choice, but you won’t want one. You have no idea, yet, slut, what I can make you do, make you want, make you feel. But you will.”

Dean felt the demon sliding down onto his cock, surrounding him with tight wet heat. At least, he thought, it’s a female demon. But then he felt something poking up into his anus, not a finger, too large; hot, and solid, and his hips were being raised off the bed to accommodate, and his ass cheeks spread wide apart, and although he still could feel the demon riding him, he could also feel a hard, long, thick, hot cock sliding into him, and somehow he knew it was all just the one demon.

Dean writhed helplessly, whimpering behind the gag, twisting on the sheets, trying to buck the demon off, or out, or in anyway to move the demon who was somehow simultaneously fucking him and being fucked by him, and it was too much, yet not enough, and it was awful and wonderful, and hideous, all at the same time. There was no pain, none at all. The demon was slow and gentle and careful, but implacable.

“That’s it, baby. Feel it, feel me, around you, within you, there’s no escape from me, from the way I make you feel. It feels good, doesn’t it, slut? Nod your head, Dean, to tell me it feels good.”

Dean didn’t want to, but it did feel good, and he felt himself nodding obediently, without volition.

“Such a good little whore.” Even as the demon was speaking, Dean felt something, mouths, hot and wet and tender, sucking gently on his nipples, both at once, and yet he could hear the demon’s words clearly. Dean sobbed, his back arching involuntarily. “Yes, pet, that’s it, very good, arch for me, feel what I do, respond, give me your responses, all your hot little noises, the arch of your back, those pretty tears, it’s all so delicious.” The demon hummed its pleasure, and Dean whimpered, unable to deny the demon anything.

***

**Notes for the Chapter:**

> No art, as this ran a little long. 
> 
> Please, please comment! Comments are life! ;)


	16. No Regrets

The invisible demon patted Dean’s head gently. “Such a good little slut. I believe I’ll have a word with Anandas, make sure that you’ll always be available to me when I come in. Thank you, pet. I am well fed and content.”

Dean shivered, kneeling on the floor of the sex work room. As promised, the invisible demon had made him beg, had made him feel every ounce of shame possible, but had not physically harmed him in the slightest. “Am I permitted to know your name?” he asked, eyes lowered respectfully, as he’d been trained by Alastair.

“Ah, of course, pet. My name is Abaddon.”

There was a knock at the door. “Come in,” Abaddon called.

Anandas opened the door and stuck his head in. “Dean, it’s time for your break. Are you done with him, Abaddon?”

“I am, for now. But I wanted a word with you on that subject, Andy. I’d like this whore - Dean, you said? - here to be available to me whenever I come in. Can we have an arrangement to that effect?”

“Technically, Dean doesn’t belong to the brothel, his soul is owned by Alastair. He’s on loan through the brothel’s contract with the Committee. So, he’s not here all the time, and I can’t guarantee that he’ll be available whenever you come in, Abby. But I can make him available to you when he is.”

“That works.” Abaddon stroked a finger over Dean’s forehead, down the side of his face, and then used it to tip up his chin. “So pretty. Thank you, Dean. Have a good break, pet.” 

Dean shivered again, as he somehow suddenly felt the demon’s absence.

“You all right, Dean?” Anandas asked.

Dean nodded. “Who  _ was  _ that?”

“Abaddon. Knight of Hell. She ranks just below the four Princes, Lilith, and Lucifer. I can’t deny her anything, Dean. If she wants you, she gets you.”

Dean nodded again. “I get it. Were you really short-handed, or did she ask for me specifically?”

“I was really short-handed. And… she might have mentioned seeing you on her way in, and how pretty she thought you were.”

Dean sighed softly. “Yeah, okay.” He rose slowly, a little stiff from kneeling for the last little while, but otherwise physically unharmed. “Break time, you said?”

“Yeah. Take twenty, why don’t you? You look like you could use it. Rehydrate. Come back to the bar when you’re ready. Here.” Anandas slipped the wristbands back onto Dean’s wrists, then snapped his fingers, and Dean found himself clad again in the jeans he’d worn to pretend to do “inventory” when Abraxas asked after him.

“Jeans? Not the booty shorts?” 

“Hey, like I said the last time, you’re just as hot in jeans. The female demons like looking at you. Some of them mentioned liking the way the jeans framed your ass.”

Dean snorted a laugh. “Great.”

“Yeah, yeah. Go on, go get some water. See you in twenty.”

***

Mark came into the break room while Dean was sitting on the couch, drinking his water. He came over, sat on the floor in front of Dean, looked up at him, and woofed softly, then nosed at Dean’s knee gently.

Dean chuckled and petted Mark’s head softly. “Hey, buddy.” Dean leaned down and gave Mark a gentle hug. Mark pressed up against Dean, cuddling, and Dean found himself weeping, the tears sinking into the wolf’s fur. Mark didn’t move, just let Dean sob. After a few moments, Dean sniffled, and sat up slowly, wiping his eyes. Mark woofed softly again, this time a question.

“Yeah, I’m okay, bud. Thank you.” 

Mark settled at Dean’s feet, curled around them as if to lend his warmth to his friend. Dean bent and gave Mark’s ears a gentle scratch and pat, then leaned back against the couch, now and then sipping slowly on his water, and let himself relax slowly, still coming down from the toxic high of the shame spiral that Abaddon had forced upon him. As promised, everything the invisible demon had done had felt incredibly good… and hideously horrible, all at once. He didn’t want to like it, but he couldn’t resist it. He didn’t want to beg for it, but hadn’t been able to stop himself when instructed to do so. He hated Abaddon… and wanted her to return as soon as possible.

Mark got up from the floor and woofed softly at him. 

“Time to go back to work, huh, bud? Okay. Thanks.” Dean patted Mark’s head gently, and the wolf’s tongue lolled out of his mouth affectionately.

***

Sensory deprivation later, when Anandas put him in it after his shift, was blessedly total. Dean shied away from thoughts of his encounter with Abaddon. He tried to focus on memories of Sammy, back when they were just kids, spending time at Bobby’s between trips with their father. 

He tried to focus on his memories of Bobby, learning to play catch, instead of shooting at set-up targets for training purposes. Bobby had always just let him be just a kid. He could relax at Bobby’s. Probably why John never left them there for long. He’d heard them fighting over the phone, once. Bobby had been a little loud, so Dean had quietly picked up the extension, and listened in. Bobby had stood up for him, told John to let him just be, told John that Dean and Sam could stay with him, go to the same school all year...and it hadn’t made a dent. John had just said, “Have them ready to go when I get there, Bobby,” and that was that.

And then John had come to get them, and Bobby had taken him out back. He’d tried to talk to John, practically begged John to let them stay. But John just shook his head, came back in, told them to get their things and get in the car. And off they went. And Dean had no idea why. It’s not like John wanted them around. He’d ditch them in a motel for weeks on end, or leave them with Pastor Jim for a few days, or with some other friend of his. But Bobby’s became only a last resort, after that. 

When Dean was old enough to take the GED test, he’d dropped out of school and helped John with hunting full time. John had made clear that education wasn’t to be Dean’s priority. He’d tried to make the same clear to Sam, but Sam… well, Sam was just different. Dean was proud of Sam for that. He’d stood up to John, gone to school, graduated from high school, gotten a full ride to Stanford, and gone there for 3 years, straight As, good test scores, would likely have been admitted to their law school with a full ride there as well, if Dean hadn’t come for him near the start of his senior year. If John hadn’t gone missing. If Jess hadn’t died. 

If Dean hadn’t been too weak to do it on his own. He’d needed Sam. Not to do research, not to back him up physically in a fight. Emotionally. Sammy had always been the stronger of the two of them emotionally. Where Dean soldiered through and just didn’t process his emotions, burying the feelings as far down as he could, Sam had somehow figured out how to actually handle things. Dean envied him that.

Dean couldn’t regret the deal he’d made that had brought him here; it had saved Sam’s life. Dean was still haunted by the vision of Jake Talley cutting through Sam’s kidneys and spinal cord and then sprinting off, Bobby on his tail, while Dean gathered Sam in his arms and tried to deny what he already knew - that Sam was dead already, dead before he’d finished falling to the ground, because bleeding out from the kidneys is quick. 

_ Dean and Sam, after Jake stabbed Sam  _

Dean couldn’t let that go, couldn’t let his brother die. 

And honestly, yeah, Hell sucked, but it was better for Dean to be here than for Sam to be dead. 

Sam being dead while Dean was still alive?  _ That _ was the real Hell. 

Being tortured and raped by demons and having to work in a brothel’s lounge bar? Pfft.

***

**Notes for the Chapter:**

> Please comment!!!???


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